Name: 80149-80-0|4-Nitrophenyl (2-(trimethylsilyl)ethyl) carbonate|97%
Brand: Ambeed
SKU: A229619
Price: 11.0 USD
Availability: InStock
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1
[ 2047-89-4 ]
[ 80149-80-0 ]
[ 108940-02-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1986,p. 2181 - 2186

2
[ 80149-80-0 ]
[ 155055-91-7 ]
[ 155055-93-9 ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 3716 - 3725

3
[ 80149-80-0 ]
[ 155055-92-8 ]
[ 155055-94-0 ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 3716 - 3725

4
[ 2916-68-9 ]
[ 7693-46-1 ]
[ 80149-80-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With pyridine; for 18h;	2-trimethylsilylethanol (25.1 mmol, 3.0 g) was reacted with p-nitrophenyl chloroformate (27.6 mmol, 5.74 g) in pyridine (60 mmol, 4.9 ml) for 18 hours, then concentrated and purified by column chromatography using silicon dioxide gel, eluting with 20 % ethyl acetate in petroleum ether to afford 4-nitrophenyl 2-(trimethylsilyl)ethyl carbonate (5.89 g, 82 % yield).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 735 - 738
[2]Journal of Organic Chemistry,1983,vol. 48,p. 1539 - 1541
[3]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 608 - 612
[4]Patent: WO2019/40104,2019,A2 .Location in patent: Paragraph 00229; 00230
[5]Journal of the Chemical Society. Perkin transactions I,1986,p. 2181 - 2186
[6]Patent: WO2018/149419,2018,A1 .Location in patent: Paragraph 001255

5
[ 80149-80-0 ]
[ 98224-26-1 ]
[ 164075-40-5 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1942 - 1954

6
[ 80149-80-0 ]
[ 56-69-9 ]
3-(5-Hydroxy-1H-indol-3-yl)-2-(2-trimethylsilanyl-ethylamino)-propionic acid [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 6965 - 6972

7
[ 80149-80-0 ]
[ 105047-45-8 ]
[ 122903-68-8 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 8415 - 8426

8
[ 80149-80-0 ]
[ 243865-46-5 ]
[ 243865-47-6 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6041 - 6048

9
[ 80149-80-0 ]
[ 243865-38-5 ]
[ 243865-39-6 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6041 - 6048

10
[ 13325-10-5 ]
[ 80149-80-0 ]
[ 351016-76-7 ]

Reference： [1]Synthesis,2001,p. 877 - 884
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 5745 - 5754

11
[ 80149-80-0 ]
[ 156-87-6 ]
[ 81616-21-9 ]

Reference： [1]Synthesis,2001,p. 877 - 884
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 5745 - 5754
[3]Tetrahedron,2005,vol. 61,p. 6046 - 6055

12
[ 2508-29-4 ]
[ 80149-80-0 ]
[ 401601-01-2 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5745 - 5754

13
[ 4048-33-3 ]
[ 80149-80-0 ]
[ 401601-02-3 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 12636 - 12643
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 5745 - 5754

14
[ 19008-71-0 ]
[ 80149-80-0 ]
[ 401601-04-5 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5745 - 5754

15
[ 80149-80-0 ]
[ 141-43-5 ]
[ 162406-69-1 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5745 - 5754

16
[ 80149-80-0 ]
[ 501027-26-5 ]
[ 501027-27-6 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 309 - 312

17
[ 80149-80-0 ]
[ 637742-76-8 ]
[ 637742-82-6 ]

Reference： [1]Synlett,2003,p. 2042 - 2046
[2]Tetrahedron,2004,vol. 60,p. 5613 - 5622

18
[ 80149-80-0 ]
[ 637742-78-0 ]
[ 637742-84-8 ]

Reference： [1]Synlett,2003,p. 2042 - 2046
[2]Tetrahedron,2004,vol. 60,p. 5613 - 5622

19
[ 80149-80-0 ]
[ 637742-77-9 ]
[ 637742-83-7 ]

Reference： [1]Synlett,2003,p. 2042 - 2046
[2]Tetrahedron,2004,vol. 60,p. 5613 - 5622

20
[ 40064-34-4 ]
[ 80149-80-0 ]
[ 181701-30-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; triethylamine; In acetonitrile; for 2h;Heating / reflux;	A solution of 13.55 g (88.21 mmol) of 4-piperidone monohydrate hydrochloride (25 g, 88.22 MMOL), 2-TRIMETHYLSILYLETHYL p-nitrophenylcarbonate (50 mL, 359.7 mmol), triethylamine (50 mL, 0.345 mol) and DMAP (10.78 g, 88.24 mmol) in 300 mL of acetonitrile is warmed under reflux for 2 hours and then allowed to cool to room temperature. The mixture is diluted with 300 ML of dichloromethane and washed 3 X 100 mL of 1 M HCI and 4 X 100 ML of 1M NAOH until all of the yellow color is removed from the organic phase. The organic phase is then washed with brine and dried over MGSO4. The organic phase is CONCENTRATED IN VACUO. to afford 19.35 g (90%) of the title. COMPOUND AS A COLORLESS OIL. 'H NMR (CDC13) 8 4.22 (M, 2 H), 3.75 (T, 4 H, J= 6.2 HZ), 2.44 (T, 4 H, J 6. 2 HZ), 1.02 (M, 2 H), 0.04 (s, 9 H).

Reference： [1]Patent: WO2004/60884,2004,A1 .Location in patent: Page 19
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2859 - 2872

21
[ 954152-92-2 ]
[ 80149-80-0 ]
[ 954153-03-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0℃; for 96.25h;	<strong>[80149-80-0]2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate</strong> (8.94 g, 31.6 mmol) was added to a solution of E67A (11.4 g, 31.5 mmol) and diisopropylethylamine (4.06 g, 5.50 mL, 31.6 mmol) in THF (55 mL) stirred at 0 C. After 15 min, the ice bath was removed. After 1d, additional <strong>[80149-80-0]2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate</strong> (2.72 g, 9.6 mmol) and diisopropylethylamine (1.65 mL, 9.6 mmol) were added and the reaction was stirred for an additional 3 d. The reaction was transferred to a separatory funnel with dichloromethane and water. The mixture was extracted with dichloromethane (2×). The combined organic layers were washed with water, dried over MgSO4 and concentrated to afford 24.1 g of crude product. Purification of the residue over silica gel eluting with ethyl acetate/dichloromethane afforded E69A (11.2 g, 70% yield): HPLC (method 7) tR=2.20 min; LCMS (ESI, pos. ion spectrum) m/z 507 (M+H).

Reference： [1]Patent: US2007/249583,2007,A1 .Location in patent: Page/Page column 135

22
[ 433939-79-8 ]
[ 80149-80-0 ]
[ 433939-80-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In tetrahydrofuran; water; for 24h;	To a suspension of [BOC-AZE-NH-CH2-((5-AMIDINO)-2-PYRIMIDINYL)] x [HOAC] (0.95 g, 2.41 mmol; see step (v) above) in 50 mL of THF was added a solution of Teoc-p-nitrophenyl carbonate (0.85 g, 3.0 mmol) and potassium carbonate (1.0 g, 7.2 mmol) in 10 mL of water. The mixture was stirred for 24 h, concentrated and partitioned between water and methylene chloride. The organic layer was washed twice with saturated aqueous sodium bicarbonate, dried [(NA2SO4)] and evaporated. The crude product was flash chromatographed on silica gel with heptane: EtOAc (1: 1). Yield: 1.04 g (90%). 'H NMR (300 MHz, [CDCI3)] [5] 9.16 (s, 2H), 4.80 (d, 2H), 4.73 (m, 1H), 4.26 (m, 2H), 4.0- 3.8 (m, 2H), 2.6-2. 4 (m, 2H), 1.47 (s, 9H), 1.12 (m, 2H), 0.07 (s, 9H)

Reference： [1]Patent: WO2003/101956,2003,A1 .Location in patent: Page 124

23
[ 433940-10-4 ]
[ 80149-80-0 ]
[ 433940-11-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate; In tetrahydrofuran; water;	To a suspension [OF BOC-PAB] (2,5-diF) x [HOAC] (0.80 g, 2.3 mmol; see step (ix) above) in 50 mL of THF was added 2- (trimethylsilyl) ethyl p-nitrophenyl carbonate (0.85 g, 3.0 mmol). A solution of potassium carbonate (0.80 g, 5.8 mmol) in 10 mL of water was added dropwise. The mixture was stirred overnight. The excess Teoc reagent was destroyed by addition of glycine (0.100 g) and potassium carbonate (0.75 g) to the solution, letting it react for an additional 2 h. The THF was evaporated and the residue was partitioned between water and methylene chloride. The aqueous layer was extracted with methylene chloride and the combined organic phase was washed with water, dried [(NA2SO4)] and evaporated. Flash chromatography on silica gel with heptane: EtOAc (2: 1) gave 0.72 g (72%) of pure compound. 'H NMR (400 MHz, CDCl3) [5] 8.00 (dd, 1H), 7.15 (dd, [1H),] 4.98 (broad, [I H),] 4.36 (bd, 2H), 4.24 (m, 2H), 1.45 (s, 9H), 1.12 (m, 2H), 0.07 (s, 9H)

Reference： [1]Patent: WO2003/101956,2003,A1 .Location in patent: Page 141; 142

24
[ 433939-96-9 ]
[ 80149-80-0 ]
[ 433939-97-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate; In tetrahydrofuran; water;	To a solution [OF BOC-PAB] (2,6-diF) x [HOAC] (1.56 g, 5.49 mmol; see step (ix) above) in 100 mL of THF and 1 mL of water was added 2- (trimethylsilyl) ethyl p-nitrophenyl carbonate (1.67 g, 5.89 mmol). A solution of potassium carbonate (1.57 g, 0.0114 mol) in 20 mL of water was added dropwise over 5 min. The mixture was stirred overnight. The THF was evaporated and the residue was partitioned between water and methylene chloride. The aqueous layer was extracted with methylene chloride and the combined organic phase was washed twice with aqueous sodium bicarbonate, dried (Na2SO4) and evaporated. Flash chromatography on silica gel with heptane/EtOAc = 2/1 gave 1.71 g (73%) of pure compound. 'H NMR (400 MHz, [CDCI3)] 8 7.43 (m, 2H), 4.97 (broad, 1H), 4.41 (broad, 2H), 4.24 (m, 2H), 1.41 (s, 9H), [1.] [11 (M,] 2H), 0.06 (s, 9H)

Reference： [1]Patent: WO2003/101956,2003,A1 .Location in patent: Page 134

25
[ 433939-96-9 ]
[ 80149-80-0 ]
[ 433939-97-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate; In tetrahydrofuran; water;	To a solution of Boc-Pab (2,6-diF) x [HOAC] (1.56 g, 5.49 mmol; see step (ix) above) in 100 mL of THF and 1 mL of water was added 2- (trimethylsilyl) ethyl p- nitrophenyl carbonate (1.67 g, 5.89 mmol). A solution of potassium carbonate (1.57 g, 0.0114 mol) in 20 mL of water was added dropwise over 5 min. The mixture was stirred overnight. The THF was evaporated and the residue was partitioned between water and methylene chloride. The aqueous layer was extracted with methylene chloride and the combined organic phase was washed twice with aqueous sodium bicarbonate, dried [(NA2S04)] and evaporated. Flash chromatography on silica gel with heptane/EtOAc = [2/1] gave 1.71 g (73%) of pure compound. [1H] NMR (400 MHz, [CDC13)] [8] 7.43 (m, 2H), 4.97 (broad, 1H), 4.41 (broad, 2H), 4.24 (m, 2H), 1.41 (s, 9H), 1.11 (m, 2H), 0.06 (s, 9H)
73%	With potassium carbonate; In tetrahydrofuran; water;	To a solution of Boc-Pab (2,6-diF) x HOAc (1.56 g, 5.49 mmol; see step (ix) above) in 100 mL of THF and 1 [ML] of water was added 2- (trimethylsilyl) ethyl p- nitrophenyl carbonate (1.67 g, 5.89 mmol). A solution of potassium carbonate (1.57 g, 0.0114 mol) in 20 [ML] of water was added dropwise over 5 min. The mixture was stirred overnight. The THF was evaporated and the residue was partitioned between water and methylene chloride. The aqueous layer was extracted with methylene chloride and the combined organic phase was washed twice with aqueous sodium bicarbonate, dried [(NA2S04)] and evaporated. Flash chromatography on silica gel with heptane/EtOAc = 2/1 gave 1.71 g (73%) of pure compound. [TH] NMR (400 MHz, [CDCL3)] [6] 7.43 (m, 2H), 4.97 (broad, 1H), 4.41 (broad, 2H), 4.24 (m, 2H), 1.41 (s, 9H), 1. [11] (m, 2H), 0.06 (s, 9H)
73%	With potassium carbonate; In tetrahydrofuran; water;	To a solution of Boc-Pab (2,6-diF) x [HOAC] (1.56 g, 5.49 mmol; see step (ix) above) in 100 mL of THF and 1 mL of water was added 2- (trimethylsilyl) ethyl p- nitrophenyl carbonate (1.67 g, 5.89 mmol). A solution of potassium carbonate (1.57 g, 0.0114 mol) in 20 mL of water was added dropwise over 5 min. The mixture was stirred overnight. The THF was evaporated and the residue was partitioned between water and methylene chloride. The aqueous layer was extracted with methylene chloride and the combined organic phase was washed twice with aqueous sodium bicarbonate, dried [(NA2SO4)] and evaporated. Flash chromatography on silica gel with heptane/EtOAc = 2/1 gave 1.71 g (73%) of pure compound. 'H NMR (400 MHz, [CDC13)] 8 7.43 (m, 2H), 4.97 (broad, 1H), 4.41 (broad, 2H), 4.24 (m, 2H), 1.41 (s, 9H), 1.11 (m, 2H), 0.06 (s, 9H)

Reference： [1]Patent: WO2003/101957,2003,A1 .Location in patent: Page 37-38
[2]Patent: WO2003/101423,2003,A1 .Location in patent: Page 28
[3]Patent: WO2003/101424,2003,A1 .Location in patent: Page 30

26
[ 1245355-46-7 ]
[ 80149-80-0 ]
Boc-Aze-Pab(Teoc) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In tetrahydrofuran; water; for 72h;	(iii) Boc-Aze-Pab(Teoc) Teoc-p-nitrophenyl carbonate (3.5 g; 12.3 mmol) was added to a solution of Boc-Aze-Pab x HCOOH (3.7 g; 10 mmol; from step (ii) above) in THF (100 mL) whereafter a solution of K2CO3 (1.8 g; 13 mmol) in water (20 mL) was added over 2 minutes. The resultant solution was stirred for 3 days, concentrated, and the remainder was taken up in EtOAc (150 mL) and NaOH (aq.; 0.5M; 50 mL). The organic layer was washed with brine (2 x 50 mL), dried (Na2SO4) and concentrated. The crude product was purified using flash chromatography (Si-gel; methylene chloride:acetone; 4:1). Yield 4.6 g (96%). 1H-NMR (500 MHz; CDCl3): delta 7.86 (d, 2H); 7.39 (d, 2H); 4.72 (bt, 1H); 4.7-4.5 (br, 2H); 3.93 (m, 1H); 3.81 (m, 1H); 2.48 (br, 2H); 1.43 (s, 9H); 0.09 (s, 9H)

Reference： [1]Patent: EP1140820,2004,B1 .Location in patent: Page 27

27
[ 80149-80-0 ]
[ 151860-17-2 ]
[ 845626-26-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate; In ethanol; water; at 20℃; for 17.5h;Heating / reflux;	[0258] 2-(Trimethylsilyl)ethyl p-nitrophenyl carbonate (2.26 g, 7.97 mmol) in abs. ethanol (10 mL) was added to a stirred suspension of compound 101b (1.50 g, 7.97 mmol, J. Chem. Soc., Perkin Trans. 1 2000: 1615-22) in aq. Na2CO3 (20 mL, 2M). Water (10 mL) was added and the sides of the flask were rinsed with abs. ethanol (15 mL). The reaction was refluxed with stirring for 1 hour, cooled, and then stirred under an atmosphere of N2 at ambient temperature for 16.5 hours. Most of the solvent was removed in vacuo and the resulting slurry was partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride (×3). The organic layers were combined and dried over Na2SO4. Filtration followed by removal of the solvent in vacuo yielded a residue that was purified via flash chromatography (19:1, methylene chloride:methanol) to yield compound 101b (2.12 g, 80% yield) as a light brown oil, 1H NMR (CDCl3, 300 MHz): 0.03 (s, 9H), 0.97 (t,j=8.3 Hz, 2H), 1.50 (s, 2H), 2.38 (d,j=8.9 Hz, 2H), 2.92 (s, 1H), 3.06 (d,j=5.9 Hz, 2H), 3.55 (s, 2H), 4.14 (t,j=8.2 Hz, 2H), 4.64 (bs, 1H), 7.19-7.30 (m, 5H); ESI(+) MS:333(M+H+).
80%	With sodium carbonate; In ethanol; water; at 20℃; for 17.5h;Heating / reflux;	2-(Trimethylsilyl)ethyl p-nitrophenyl carbonate (2.26 g, 7.97 mmol) in abs. ethanol (10 mL) was added to a stirred suspension of compound 201 (1.50 g, 7.97 mmol, J. Chem. Soc., Perkin Trans. 1 2000: 1615-22) in aq. Na2CO3 (20 mL, 2M). Water (10 mL) was added and the sides of the flask were rinsed with abs. ethanol (15 mL). The reaction was refluxed with stirring for 1 hour, cooled, and then stirred under an atmosphere of N2 at ambient temperature for 16.5 hours. Most of the solvent was removed in vacuo and the resulting slurry was partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride (×3). The organic layers were combined and dried over Na2SO4. Filtration followed by removal of the solvent in vacuo yielded a residue that was purified via flash chromatography (19:1, methylene chloride:methanol) to yield compound 202 (2.12 g, 80% yield) as a light brown oil, 1H NMR (CDCl3, 300 MHz): 0.03 (s, 9H), 0.97 (t, J=8.3 Hz, 2H), 1.50 (s, 2H), 2.38 (d, J=8.9 Hz, 2H), 2.92 (s, 1H), 3.06 (d, J=5.9 Hz, 2H), 3.55 (s, 2H), 4.14 (t, J=8.2 Hz, 2H), 4.64 (bs, 1H), 7.19-7.30 (m, 5H); ESI(+) MS: 333 (M+H+).

Reference： [1]Patent: US2005/43298,2005,A1 .Location in patent: Page/Page column 25
[2]Patent: US2005/197333,2005,A1 .Location in patent: Page/Page column 29

28
4(R)-(3-methoxycarbonylphenyl)-3(R),4-dimethyl-1-piperidine hydrochloride [ No CAS ]
[ 80149-80-0 ]
[ 762299-42-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-ethyl-N,N-diisopropylamine; In acetonitrile;	4(R)-(3-methoxycarbonylphenyl)-3(R),4-dimethyl-1-(2-trimethylsilylethyloxycarbonyl) Piperidine (6) To a suspension of 5 (1.31 g, 0.0046 mol, 1 eq) in anhydrous acetonitrile (15 mL) was added diisopropylethylamine (1.68 mL, 0.0096 mol, 2.1 eq) and 2-(trimethylsilyl)ethyl-p-nitrophenylcarbonate (1.44 g, 0.0050 mol, 1.1 eq). The resulting solution was concentrated under vacuum and ethyl acetate (200 mL) was added. The organic layer was washed with aqueous 1N NaOH (100 mL), aqueous 1N HCl (100 mL), water (100 mL), brine (100 mL), dried over sodium sulfate and concentrated under vacuum. Purification of the crude product by column chromatography (eluent:hexane/ethyl acetate=95:5) afforded the title compound (1.67 g, 92%).

Reference： [1]Patent: US2004/186135,2004,A1 .Location in patent: Page/Page column 18; 22

29
C₁₄H₂₀N₂ [ No CAS ]
[ 80149-80-0 ]
[ 845626-27-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol; water; at 20℃; for 20h;Heating / reflux;	[0269] 2-(Trimethylsilyl)ethyl p-nitrophenyl carbonate (2.53 g, 8.92 mmol) in abs. ethanol (25 mL) was added to a stirred suspension of compound 102b (U.S. Pat. No. 5,654,318, 1.93 g, 8.92 mmol) in aq. Na2CO3 (20 mL, 2M), followed by the addition of water (10 mL). The reaction was refluxed with stirring for 1 hour, cooled, and then stirred under an atmosphere of N2 at ambient temperature for 19 hours. Most of the solvent was removed in vacuo and the resulting slurry was partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride (×2). The organic layers were combined and dried over Na2SO4. Filtration followed by removal of the solvent in vacuo yielded a residue that was purified via flash chromatography (19:1, methylene chloride:methanol) to yield compound 102a (2.59 g, 80% yield) as a light brown oil, 1H NMR (CDCl3, 300 MHz): 0.03 (s, 9H), 0.95-1.01 (m, 2H), 1.38-1.76 (m, 5H), 2.13-2.15 (m, 1H), 2.50 (d,j=8.9H), 2.61-2.67 (m, 1H), 2.73-2.87 (m, 3H), 3.66 (dd,j=21.5, 13.1 Hz, 2H), 3.93 (bs, 1H), 4.12-4.17 (m, 2H), 4.62 (bs, 1H), 7.22-7.31 (m, 5H); ESI (+) MS: 361 (M+H+).

Reference： [1]Patent: US2005/43298,2005,A1 .Location in patent: Page/Page column 26

30
(1R,5S)-3-benzyl-3,8-diazabicyclo[3.2.1]octane [ No CAS ]
[ 80149-80-0 ]
C₁₉H₃₀N₂O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 17.5h;	[0289] 2-(Trimethylsilyl)ethyl p-nitrophenyl carbonate (1.35 g, 4.78 mmol) in acetonitrile (10 mL) was added to a stirred solution of compound 104b (Tet. Lett. 2002, 899-902, 920 mg, 4.55 mmol), and diisopropylethylamine (0.833 mL, 4.78 mmol) in acetonitrile (10 mL). The reaction was stirred at ambient temperature for 17.5 hours. The solvent was removed in vacuo and the resulting residue was dissolved in ethyl acetate and washed with 1M NaOH (×4), water (×2), then brine (×1), and dried over Na2SO4. Filtration, followed by removal of the solvent in vacuo, gave a residue that was purified via flash chromatography (1:4, ethyl acetate:hexanes, then 1:9 ethyl acetate:hexanes) to produce compound 104a (664 mg, 42% yield) as a colorless oil, 1H NMR (CDCl3, 300 MHz): 0.03 (s, 9H), 0.96-1.02 (m, 2H), 1.80-1.95 (m, 4H), 2.29 (bs, 2H), 2.59-2.64 (m, 2H), 3.46 (s, 2H), 4.15-4.29 (m, 4H), 7.21-7.30 (m, 5H); ESI (+) MS: 347 (M+H+).
42%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 17.5h;	2-(Trimethylsilyl)ethyl p-nitrophenyl carbonate (1.35 g, 4.78 mmol) in acetonitrile (10 mL) was added to a stirred solution of compound 207 (Tet. Lett. 2002, 899-902, 920 mg, 4.55 mmol), and diisopropylethylamine (0.833 mL, 4.78 mmol) in acetonitrile (10 mL). The reaction was stirred at ambient temperature for 17.5 hours. The solvent was removed in vacuo and the resulting residue was dissolved in ethyl acetate and washed with 1M NaOH (×4), water (×2), then brine (×1), and dried over Na2SO4. Filtration, followed by removal of the solvent in vacuo, gave a residue that was purified via flash chromatography (1:4, ethyl acetate:hexanes, then 1:9 ethyl acetate:hexanes) to produce compound 208 (664 mg, 42% yield) as a colorless oil, 1H NMR (CDCl3, 300 MHz): 0.03 (s, 9H), 0.96-1.02 (m, 2H), 1.80-1.95 (m, 4H), 2.29 (bs, 2H), 2.59-2.64 (m, 2H), 3.46 (s, 2H), 4.15-4.29 (m, 4H), 7.21-7.30 (m, 5H); ESI(+) MS: 347 (M+H+).

Reference： [1]Patent: US2005/43298,2005,A1 .Location in patent: Page/Page column 27-28
[2]Patent: US2005/197333,2005,A1 .Location in patent: Page/Page column 32

31
[ 853181-94-9 ]
[ 80149-80-0 ]
[ 853181-96-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In tetrahydrofuran; at 70℃; for 6h;	B. 2- (Trimethylsilyl) ethyl 5- (4-fluorophenyl)-6- (hydroxymethyl)-7- (1- methylethyl)-3, 4-dihydro-1, 8-naphthyridine-1 (2H)-carboxylate. To a solution of the compound of Part A (3.1 g, 10.3 mmol) in THF (20mL) were added triethylamine (2.09 g, 20.7 mmol, 2.0 equiv) and 4-nitrophenyl 2- (trimethylsilyl) ethyl carbonate (4.09 g, 14.5 mmol, 1.4 equiv). The reaction was heated at70 C for 6 h, cooled to room temperature, and mixed with ethyl acetate (100 mL). This mixture was then washed successively with 2 x 100mL each of saturated ammonium chloride then saturated sodium bicarbonate, followed by drying with magnesium sulfate and concentration. Purification by silica gel chromatography eluting with 0.5% methanol in methylene chloride gave 2- (trimethylsilyl) ethyl5- (4- fluorophenyl)-6- (hydroxymethyl)-7- (1-methylethyl)-3, 4-dihydro-1, 8-naphthyridine- 1 (2H) -carboxylate (3.56 g, 8.0 mmol, 78%) as an off-white foam : LC-MS (ESI, pos. ion spectrum) m/z 445 (M+H); LC method 1,tR = 1.69 min.

Reference： [1]Patent: WO2005/51386,2005,A1 .Location in patent: Page/Page column 114

32
[ 433939-79-8 ]
[ 80149-80-0 ]
Boc-Aze-NH-CH₂-[(5-(amino(trimethylsilylethylimino)methyl))-2-pyrimidinyl] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In tetrahydrofuran; water; for 24h;	To a suspension of Boc-Aze-NH-CH2-((5-amidino)-2-pyrimidinyl)*HOAc (0.95 g, 2.41 mmol; see step (v) above) in 50 mL of THF was added a 5 solution of Teoc-p-nitrophenyl carbonate (0.85 g, 3.0 mmol) and potassium carbonate (1.0 g, 7.2 mmol) in 10 mL of water. The mixture was stirred for 24 h, concentrated and partitioned between water and methylene chloride. The organic layer was washed twice with saturated aqueous sodium bicarbonate, dried (Na2SO4) and evaporated. The crude product was flash chromatographed on silica gel with heptane:EtOAc (1:1). Yield: 1.04 g (90%). 1H NMR (300 MHz, CDCl3) delta9.16 (s, 2H), 4.80 (d, 2H), 4.73 (m, 1H), 4.26 (m, 2H), 4.0-3.8 (m, 2H), 2.6-2.4 (m, 2H), 1.47 (s, 9H), 1.12 (m, 2H), 0.07 (s, 9H)

Reference： [1]Patent: US2004/19033,2004,A1 .Location in patent: Page/Page column 44

33
[ 866467-38-1 ]
[ 80149-80-0 ]
[ 1131006-67-1 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1723 - 1730
[2]Patent: WO2005/94818,2005,A1 .Location in patent: Page/Page column 24

34
[ 80149-80-0 ]
[ 871553-73-0 ]

Yield	Reaction Conditions	Operation in experiment
63%		To a solution of DMF (100 mL) was added 4-amino-N-(2-methoxyethyl)-5- (4-nitrophenyl)pyrrolo[2,1-fJ[1,2,4]triazine-6-carboxamide (4.03g, 11.3 mmol) followed by 60% NaH by weight in mineral oil (1.13g, 28.3 mmol). The solution was stirred for 15 min and then 4-nitrophenyl 2- (trimethylsilyl)ethyl (3.52 g, 12.4 mmol) was added. The solution was stirred under N2 for 2 h. MeOH was added to the reaction until bubbling ceased and then EtOAc (50 mL) was added. The solution was transferred to a separatory funnel and was washed with IN NaOH (20 mL) and water (20 mL). The organic was collected, dried (Na2S04), and purified by column chromatography to afford 3.60 g of the above compound (7.15 mmol, yield 63%). (at)H-NMR (CDCl3) 8 8.38 (d, J = 8.5 Hz, 2H), 8.16 (s, 1H), 8.14 (s, 1H), 7.69 (d, J = 8.5 Hz, 2H); 5.87 to 5.86 (m, 1H), 4.17 (t, J = 8.3 Hz, 2H), 3.48 to 3.46 (m, 2H), 3.36 (t, J = 5.0 Hz 2H), 3.21 (s, 3H), 0.93 (t, J = 8.1 Hz 2H),-0.01 (s, 9H) ; MS [M+H] (at) = 501; LCMS RT = 3.17 min.

Reference： [1]Patent: WO2005/121147,2005,A1 .Location in patent: Page/Page column 86; 87

35
[ 5683-33-0 ]
4-piperidone monohydrate [ No CAS ]
[ 80149-80-0 ]
4-oxo-piperidine-1-carboxylic acid (trimethylsilyl)-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; acetonitrile;	A. 4-oxo-piperidine-1-carboxylic acid (trimethylsilyl) ethyl ester A solution of 4-piperidone monohydrate. Hydrochloride (13.55 g, 88 mmol) 2-trimethylsilylethyl-p-nitrophenylcarbonate (25.00 g, 88 mmol) in acetonitrile (300 ml) was treated with triethylamine (50 ml, 359 mmol) and dimethyl-aminopyridine (10.78 g, 88 mmol) and heated to reflux for 2 hours. The solution was cooled and concentrated to an oil. The residue was dissolved in dichloromethane (300 ml) and washed twice with 1M hydrochloric acid and twice with 1M sodium hydroxide until all of the yellow color was removed from the organics. The organics were then washed with brine, dried over magnesium sulfate and concentrated under vacuum to give 4-oxo-piperidine-1-carboxylic acid (trimethylsilyl) ethyl ester as colorless oil. (19.35 g) 1H NMR (CDCl3, 300 MHz): delta4.24 (2H, t), 3.78 (4H, t), 2.45 (4H, t), 1.05 (2H, t), 0.05 (9H, s) MS (EI) 284(M+CH3CN).

Reference： [1]Patent: US2003/187020,2003,A1

36
[ 41979-39-9 ]
[ 80149-80-0 ]
[ 181701-30-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine;dmap; In acetonitrile; for 2h;Reflux;	A. 4-Oxo-piperidine-1 -carbox lic acid 2-trimethylsilanyl-ethyl esterA solution of 4-piperidone monohydrate hydrochloride (25 g, 88.22 mmol), 2- trimethylsilylethyl p-nitrophenylcarbonate (50 mL, 359.7 mmol), triethylamine (50 mL, 0.345 mol) and DMAP (10.78 g, 88.24 mmol) in acetonitrile (300 mL) is warmed under reflux for 2 hours and then allowed to cool to room temperature. The mixture is diluted with dichloromethane (300 mL) and washed with 1 M HCI (3x100 mL) and 1 M NaOH (4 X 100 mL) until all of the yellow color is removed from the organic phase. The organic phase is then washed with brine and dried over MgSO4. The organic phase is concentrated in vacuo to afford the title compound (19.35 g, 90%) as a colorless oil.1 H NMR (300 MHz, CDCI3) delta 4.22 (m, 2H), 3.75 (t, J = 6.2 Hz, 4H), 2.44 (t, J = 6.2 Hz, 4H), 1 .02 (m, 2H), 0.04 (s, 9H).
90%	With dmap; triethylamine; In acetonitrile; for 2h;Reflux;	A solution of 4-piperidone monohydrate hydrochloride (25 g, 88.22 mmol), 2- trimethylsilylethyl p-nitrophenylcarbonate (50 mL, 359.70 mmol), triethylamine (50 mL, 345.00 mmol) and DMAP (10.78 g, 88.24 mmol) in of acetonitrile (300 mL) is warmed under reflux for 2 hours and then allowed to cool to room temperature. The mixture is diluted with dichloromethane (300 mL) and washed 1 M HC1 (3 X 100 mL) and 1 M NaOH (4 X 100 mL) until all of the yellow color is removed from the organic phase. The organic phase is then washed with brine and dried over MgSC^. The organic phase is concentrated in vacuo to afford 19.35 g (90%) of the title compound as a colorless oil. 1H NMR (CDC13, 300 MHz) delta 4.22 (m, 2H), 3.75 (t, J = 6.2 Hz, 4H), 2.44 (t, J= 6.2 Hz, 4H), 1.02 (m, 2H), 0.04 (s, 9 H).
	With dmap; triethylamine; In acetonitrile; for 2h;Heating / reflux;	Carbonic acid 4- nitro-phenyl ester-2-trimethylsilanyl-ethyl ester (8.33 g, 29.3 mmol), triethylamine (12.3 g, 122 mmol) and DMAP (3.6 g, 29.5 mmol) were added to a room temperature solution of 4- piperidone hydrochloride (4.52 g, 33.4 mmol) in 100 mL of acetonitrile. The resulting mixture was heated at reflux for 2 h, then cooled and the volatiles were removed in vacuo. The residue was dissolved in dichloromethane, washed with water and IM NaOH solution, and concentrated in vacuo to leave 6.3 g of product.

Reference： [1]Patent: WO2011/79102,2011,A1 .Location in patent: Page/Page column 26
[2]Patent: WO2011/78984,2011,A1 .Location in patent: Page/Page column 26; 27
[3]Patent: WO2006/86705,2006,A1 .Location in patent: Page/Page column 66

37
[ 80149-80-0 ]
[ 67571-90-8 ]
[ 845626-29-1 ]

Yield	Reaction Conditions	Operation in experiment
42%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 17.5h;	2-(Trimethylsilyl)ethyl p-nitrophenyl carbonate (1.35 g, 4.78 mmol) in acetonitrile (10 mL) was added to a stirred solution of compound 104 (Tet. Lett. 2002, 899-902, 920 mg, 4.55 mmol), and diisopropylethylamine (0.833 mL, 4.78 mmol) in acetonitrile (10 mL). The reaction was stirred at ambient temperature for 17.5 hours. The solvent was removed in vacuo and the resulting residue was dissolved in ethyl acetate and washed with 1M NaOH (×4), water (×2), then brine (×1), and dried over Na2SO4. Filtration, followed by removal of the solvent in vacuo, gave a residue that was purified via flash chromatography (1:4, ethyl acetate:hexanes, then 1:9 ethyl acetate:hexanes) to produce compound 105 (664 mg, 42% yield) as a colorless oil, 1H NMR (CDCl3, 300 MHz): 0.03 (s, 9H), 0.96-1.02 (m, 2H), 1.80-1.95 (m, 4H), 2.29 (bs, 2H), 2.59-2.64 (m, 2H), 3.46 (s, 2H), 4.15-4.29 (m, 4H), 7.21-7.30 (m, 5H); ESI(+)MS: 347 (M+H+).

Reference： [1]Patent: US2007/155715,2007,A1 .Location in patent: Page/Page column 20

38
[ 172349-26-7 ]
[ 80149-80-0 ]
[ 433939-59-4 ]

Yield	Reaction Conditions	Operation in experiment
69%		Boc-Pro-Pab (Z) (see international patent application WO 97/02284,15. 0 g, 0.0321 mol) was dissolved in 150 mL of ethanol and 200 mg 10% Pd/C (50% moisture) was added. The mixture was stirred and hydrogenated at atmospheric pressure for 2 h, filtered through Hyflo and concentrated. The product was used without further purification. Of this product was taken 10 g (0.029 mol), which was dissolved in 300 mL of THF. Teoc-p-nitrophenyl carbonate (10 g, 0.035 mol) was added. A solution of potassium carbonate (5.2 g, 0.038 mol) in 50 mL of water was added over 3 min and the resulting solution was stirred for 3 days, concentrated and the remainder was extracted with EtOAc three times. The combined organic layer was washed with water, dried [(NA2SO4)] and evaporated. The crude product was flash chromatographed on silica gel using methylene chloride: acetone (4: 1). Yield: 9. [8 G] (69%).

Reference： [1]Patent: WO2003/101956,2003,A1 .Location in patent: Page 110

39
Boc-Pro-Pab(Z) [ No CAS ]
[ 80149-80-0 ]
Boc-Pro-Pab(Teoc) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		Boc-Pro-Pab(Z) (see international patent application WO 97/02284, 15.0 g, 0.0321 mol) was dissolved in 150 mL of ethanol and 200 mg 10% Pd/C (50% moisture) was added. The mixture was stirred and hydrogenated at atmospheric pressure for 2 h, filtered through Hyflo and concentrated. The product was used without further purification. Of this product was taken 10 g (0.029 mol), which was dissolved in 300 mL of THF. Teoc-p-nitrophenyl carbonate (10 g, 0.035 mol) was added. A solution of potassium carbonate (5.2 g, 0.038 mol) in 50 mL of water was added over 3 min and the resulting solution was stirred for 3 days, concentrated and the remainder was extracted with EtOAc three times. The combined organic layer was washed with water, dried (Na2SO4) and evaporated. The crude product was flash chromatographed on silica gel using methylene chloride:acetone (4:1). Yield: 9.8 g (69%).

Reference： [1]Patent: US2004/19033,2004,A1 .Location in patent: Page/Page column 39

40
[ 1043469-27-7 ]
[ 80149-80-0 ]
[ 1043469-29-9 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 9556 - 9565

41
[ 1025687-93-7 ]
[ 80149-80-0 ]
1-[2-(trimethylsilyl)ethoxy]carbonyl-5'-cyano-spiro[piperidine-4,3'-benzo[b]furan] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		Compound 1f, (4.79 g, 15.2 mmol; Example 1) was combined with trifluoroacetic acid (20 ml_) in dry dichloromethane (50 mL) and stirred at room temperature for 15 minutes. The reaction mixture was concentrated in vacuo and the residue was dissolved in acetonitrile (70 ml) and treated with 4-dimethylaminopyridine (1.9 g, 15.2 mmol), triethylamine (6.2 g, 60.8 mmol) and 4-nitrophenyl-2-(trimethylsilyl)ethyl carbonate (4.3 g, 15.2 mmol). The resulting <n="155"/>reaction mixture was refluxed for 16 hours under a nitrogen atmosphere and concentrated in vacuo. The residue was partitioned between dichloromethane (50 mL) and 1N aqueous hydrochloric acid (50 ml_). The organic phase was separated and washed twice with 1 N aqueous hydrochloric acid (50 mL) then with 1 N aqueous sodium hydroxide (50 mL). The resulting suspension was and filtered through filter agent and the organic phase was separated and extracted sequentially with 1 N aqueous sodium hydroxide (2 x 50 mL), water (50 mL), brine (50 mL), dried over sodium sulfate and concentrated in vacuo to give a thick pale yellow syrup. This syrup was recrystallized from dichloromethane/hexane to give 3.84 g (70%) of 2a as a pale yellow solid.

Reference： [1]Patent: WO2009/67202,2009,A1 .Location in patent: Page/Page column 153-154

42
[ 1001057-04-0 ]
[ 80149-80-0 ]
[ 1134561-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 64h;	(14a) (2-Bromo-5-nitrobenzyl)carbamic acid 2-trimethylsilanylethyl ester To a mixture of 2-bromo-5-nitrobenzylamine (Example (1d)) (2.77 g) and dichloromethane (80 mL) there were added triethylamine (1.72 mL) and 2-trimethylsilanylethyl 4-nitrophenyl carbonate [CAS No. 80149-80-0] (3.5 g), and the mixture was stirred at room temperature for 64 hours. Ethyl acetate (300 mL) and water (300 mL) were added to the mixture, and after sufficiently shaking, the organic layer was separated off and washed with a 1N aqueous sodium hydroxide solution (300 mL) and saturated aqueous sodium chloride (300 mL) in that order, and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (1.69 g) as a colorless solid. 1H-NMR (CDCl3) delta 0.06 (s, 9H) 1.01 (m, 2H) 4.20 (m, 2H) 4.49 (d, J=6.4 Hz, 2H) 5.26 (br.s, 1H) 7.73 (d, J=8.4 Hz, 1H) 8.00 (dd, J=8.4, 2.0 Hz, 1H) 8.25 (d, J=2.0 Hz, 1H)

Reference： [1]Patent: US2009/270433,2009,A1 .Location in patent: Page/Page column 59-60

43
[ 80149-80-0 ]
[ 161420-87-7 ]
[ 1268883-95-9 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7441 - 7451

44
[ 80149-80-0 ]
[ 181954-34-7 ]
[ 1248587-10-1 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7441 - 7451

45
[ 1262007-88-4 ]
[ 80149-80-0 ]
[ 1262008-93-4 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl 2-(6-hydroxy-2,3,4,9-tetrahydro-lH-pyrido[3,4-b]indol-l-yl)acetate (0.130 g, 0.499 mmol, see Example 1.2, Steps A and B) was suspended in dichloromethane (4.99 mL), DIEA (0.113 mL, 0.649 mmol), then TMSCl (0.160 mL, 1.249 mmol) were added at 24 0C to give an amber solution. Additional DIEA (0.113 mL, 0.649 mmol) was added, the reaction mixture was stirred for 2 h after which 2-(trimethylsilyl)ethyl/?-nitrophenyl carbonate (0.149 g, 0.524 mmol) was added at 24 0C. After 18 h DMF (4.99 mL, 0.499 mmol) was added to the reaction mixture, DCM was removed in vacuo, and the reaction mixture was stirred at 24 0C for 16 h. The solvent was concentrated at 24 0C to give an oil which was partitioned betweenEtOAc (50 mL) and water/brine (10 mL/10 mL). The organic layer was washed with brine (20 mL), dried with MgSO4, concentrated, and purified by silica gel flash chromatography to give an oil. This oil was dissolved in DCM (3 mL) and coevaporated in vacuo with hexane (10 mL) to give the title compound as a solid (0.057 g). LCMS m/z = 405.4 [M+H]+. 1H NMR (400 MHz, DMSO-Cf6) delta ppm 0.03 (s, 9 H), 0.90 - 1.05 (m, 2 H), 2.53 - 2.62 (m, 3 H), 2.70 - 2.82 (m, 1 H), 2.83 - 2.90 (m, 1 H), 3.60 (s, 3 H), 4.14 (t, J= 8.27 Hz, 2 H), 4.18 - 4.24 (m, 1 H), 6.57 (dd, J = 8.59, 2.40 Hz, 1 H), 6.69 (d, J= 2.15 Hz, 1 H), 7.09 (d, J= 8.59 Hz, 1 H), 8.58 (s, 1 H), 10.48 (s, 1 H).

Reference： [1]Patent: WO2011/5295,2011,A1 .Location in patent: Page/Page column 104; 105

46
[ 1264245-77-3 ]
[ 80149-80-0 ]
[ 1264239-29-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	(1. Alloc protection of the secondary amino group with allyloxycarbonyl-N- hydroxysuccinimide (AllocOSu) in CH2Cl2, 2. cleavage of the Boc group with dioxane-HCl;3. Teoc protection of the primary amino group with 2-(trimethylsilyl) ethyl 4-nitrophenyl carbonate (Teoc-ONp) in CH2Cl2 in the presence of Et3N) from amino alcohol 13, applying standard conditions; as leading references cf.T. W. Greene, P. G. M. Wuts, Protective Groups in OrganicSynthesis, 3rd edition, John Wiley & Sons, 1999;P.J. Kocienski, Protecting Groups, 3rd edition, Georg Thieme Verlag, 2005.Data of 16: Ci5H28N2O5Si (344.5): Flow injection MS (APCI): 689 ([2M+H]+), 345 ([M+H]+). 1H-NMR (DMSO-d6): 7.28 (d, J = 6.1, 1 H), 5.90 (m, 1 H), 5.25 (qd, J = 1.7, 17.2, 1 H), 5.16 (qd, J = 1.5, 10.5, 1 H), 4.90 (br. t, 1 H), 4.54-4.42 (m, 2 H), 4.04- 3.97 (m, 2 H), 3.90 (q, J = 6.8, 1 H), 3.80-3.66 (br. m and dd, 2 H), 3.57-3.43 (br. m, 2 H), 2.96 (br. m, 1 H), 2.19 (br. m, 1 H), 1.78 (br. m, 1 H), 0.89 (t, J ca 8.3, 2 H), 0.00 (s, 9 H)
	With triethylamine; In dichloromethane;	(2S,4S)-Allyl 2-(hydroxymethyl)-4-((2-(trimethylsilyl)ethoxy)carbonylamino)pyrrolidine-1-carboxylate (16) was prepared in three steps (1. Alloc protection of the secondary amino group with allyloxycarbonyl-N-hydroxysuccinimide (AllocOSu) in CH2Cl2, 2. cleavage of the Boc group with dioxane-HCl;3. Teoc protection of the primary amino group with <strong>[80149-80-0]2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate</strong> (Teoc-ONp) in CH2Cl2 in the presence of Et3N) from amino alcohol 13, applying standard conditions; as leading references cf. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd edition, John Wiley & Sons, 1999; P. J. Kocienski, Protecting Groups, 3rd edition, Georg Thieme Verlag, 2005.Data of 16: C15H28N2O5Si (344.5): Flow injection MS (APCI): 689 ([2M+H]+), 345 ([M+H]+). 1H-NMR (DMSO-d6): 7.28 (d, J=6.1, 1 H), 5.90 (m, 1H), 5.25 (qd, J=1.7, 17.2, 1H), 5.16 (qd, J=1.5, 10.5, 1H), 4.90 (br. t, 1H), 4.54-4.42 (m, 2H), 4.04-3.97 (m, 2H), 3.90 (q, J=6.8, 1H), 3.80-3.66 (br. m and dd, 2H), 3.57-3.43 (br. m, 2H), 2.96 (br. m, 1H), 2.19 (br. m, 1 H), 1.78 (br. m, 1H), 0.89 (t, J ca 8.3, 2H), 0.00 (s, 9H)

Reference： [1]Patent: WO2011/15241,2011,A1 .Location in patent: Page/Page column 180
[2]Patent: US2012/202821,2012,A1 .Location in patent: Page/Page column 116; 242
[3]Patent: CN105294732,2016,A .Location in patent: Paragraph 0738; 0741; 1406
[4]Patent: JP2015/155430,2015,A .Location in patent: Paragraph 0104

47
[ 58971-11-2 ]
[ 80149-80-0 ]
[ 1313605-21-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; In methanol;	Example 20A: 2-(trimethylsilyl)ethyl 3 -bromophenethylcarbamate 1003351 2-(3-Bromophenyl)ethanamine (1 g, 5.00 mmol) and 2-(trimethylsilyl)ethylp-nitrophenyl carbonate (1.416 g, 5.00 mmol) were dissolved in MeOH (40.0 mL). DIPEA (1.048 mL, 6.00 mmol) was added, and the reaction was allowed to stir overnight. The reaction was concentrated in vacuo. The crude material was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to yield Example 20A (1.61 g, 94%) 1H NMR (400 MHz, CHLOROFORM-cl) oe ppm 7.30 - 7.35 (2 H, m), 7.14 (1 H, t,J=7.53 Hz), 7.06-7.11 (1 H, m), 4.60(1 H, br. s.), 4.07-4.15 (2 H, m), 3.38 (2 H, q, J=6.61 Hz), 2.75 (2 H, t, J=6.78 Hz), 0.89 - 0.99 (2 H, m), 0.00 (9 H, s).

Reference： [1]Patent: WO2014/201073,2014,A1 .Location in patent: Paragraph 00335; 00355
[2]Chemistry - A European Journal,2011,vol. 17,p. 6973 - 6984
[3]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 67 - 72

48
[ 1337913-86-6 ]
[ 80149-80-0 ]
[ 1337913-74-2 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5704 - 5707

49
[ 1264243-41-5 ]
[ 80149-80-0 ]
[ 1266099-66-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane	2 (2S,4R)-2-(Trimethylsilyl)ethyl 4-(tert-butoxycarbonylamino)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (152) 152 was obtained by Teoc protection of the secondary amino group of 17 with 2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate (Teoc-ONp) in CH2Cl2 in the presence of Et3N applying standard conditions.Data of 152: C16H32N2O5Si (360.5). 1H-NMR (DMSO-d6): 7.03 (br. s, 1H), 4.71 (m, 1H), 4.07-4.01 (m, 3H), 3.76 (m, 1H), 3.45-3.35 (br. m, 3H), 3.11 (m, 1H), 2.00 (m, 1H), 1.75 (m, 1H), 1.36 (s, 9H), 0.91 (t, J=7.8, 2H), 0.00 (s, 9H).

Reference： [1]Current Patent Assignee: SPEXIS AG - US2012/270881, 2012, A1 Location in patent: Page/Page column 113

50
[ 17900-95-7 ]
[ 80149-80-0 ]
[ 1426243-13-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 5,6-dibromo-1H-indole-3-carboxaldehyde With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h; Inert atmosphere;

Reference： [1]Parsons, Thomas B.; Spencer, Neil; Tsang, Chi W.; Grainger, Richard S. [Chemical Communications, 2013, vol. 49, # 23, p. 2296 - 2298]

51
[ 17900-95-7 ]
[ 80149-80-0 ]
[ 1426243-18-6 ]
[ 1426243-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere 1.2: 16 h / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere 2.2: 2 h / -78 °C / Inert atmosphere

Reference： [1]Parsons, Thomas B.; Spencer, Neil; Tsang, Chi W.; Grainger, Richard S. [Chemical Communications, 2013, vol. 49, # 23, p. 2296 - 2298]

52
4-(1,3-difluoropropan-2-yloxy)-3-fluoro-5-((methylamino)methyl)aniline dihydrochloride [ No CAS ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl 5-amino-2-(1,3-difluoropropan-2-yloxy)-3-fluorobenzyl(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.3%	With N-ethyl-N,N-diisopropylamine; In methanol; at 20℃; for 3h;	j00183j Intermediate 14B (0.250 g, 0.878 mmol) and 2-(trimethylsilyl)ethyl pnitrophenyl carbonate (0.249 g, 0.878 mmol) were dissolved in MeOH (10 mL), andDIPEA (0.460 mL, 2.63 mmol) was added. The reaction was allowed to stir at rt for 3 h.The reaction was concentrated and purified through a plug of silica gel eluting with 20%EtOAc/Hex to yield Intermediate 14 (0.256 g, 0.652 mmol, 74.3 % yield). MS (ESI) m/z:365.3 (M-28) (M-28 is consistent with Teoc containing compounds). 1H NMR (400MHz, CHLOROFORM-cl) oe ppm 6.34 (2 H, dd, J=12.92, 2.64 Hz), 4.72 (2 H, dd, J=4.52,1.25 Hz), 4.60 (2 H, dd, J=4.52, 1.25 Hz), 4.49 (2 H, s), 4.21 (2 H, t, J=8.28 Hz), 2.85 (2H, br. s.), 1.21 - 1.37 (4 H, m), 1.01 (2 H, br. s.), -0.03 - 0.10 (9 H, m).

Reference： [1]Patent: WO2014/201073,2014,A1 .Location in patent: Paragraph 00183

53
(R)-2-(5-bromo-2-methoxyphenyl)-N-methylpropan-1-amine [ No CAS ]
[ 80149-80-0 ]
(R)-2-(trimethylsilyl)ethyl 2-(5-bromo-2-methoxyphenyl)propyl(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine; In methanol;	Intermediate 1 8G: (R)-2-(Trimethylsilyl)ethyl 2-(5 -bromo-2- methoxyphenyl)propyl(methyl)carbamate j00201j Intermediate 18F (107 mg, 0.4 14 mmol) and 2-(trimethylsilyl)ethyl pnitrophenyl carbonate (117 mg, 0.414 mmol) were dissolved in MeOH (3.3 mL). DIPEA (87 .iL, 0.497 mmol) was added and the reaction was allowed to stir overnight. The reaction was concentrated in vacuo at purified by silica gel column chromatography(gradient from 0 to 100% EtOAc in hexanes) to yield Intermediate 18G (0.150 g, 90%).?H NMR (400MHz, CHLOROFORM-d) oe 7.35 - 7.22 (m, 2H), 6.67 (d, J=8.8 Hz, 1H), 4.17-3.93 (m, 2H), 3.75 (s, 3H), 3.49 (dd, J=14.9, 7.7 Hz, 1H), 3.31 (d, J=7.5 Hz, 2H),2.81 - 2.69 (m, 3H), 1.15 (d, J=6.5 Hz, 3H), 0.99 - 0.83 (m, 2H), 0.00 (s, 9H).

Reference： [1]Patent: WO2014/201073,2014,A1 .Location in patent: Paragraph 00201
[2]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 67 - 72

54
2-(2-(benzyloxy)-5-bromophenyl)ethanamine hydrochloride [ No CAS ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl 2-(benzyloxy)-5-bromophenethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With N-ethyl-N,N-diisopropylamine; In methanol; at 20℃; for 2h;	Example 1 9D: 2-(Trimethylsilyl)ethyl 2-(benzyloxy)-5-bromophenethylcarbamate j00327j Example 19C (105 mg, 0.306 mmol) and 2-(trimethylsilyl)ethyl p-nitrophenyl carbonate (87 mg, 0.306 mmol) were dissolved in MeOH (1 mL) and DIPEA (0.268 mL,1.532 mmol) was added. The reaction was allowed to stir at RT for 2 h. The reaction mixture was concentrated under reduced pressure. The crude reaction mixture was purified by silica gel column chromatography (gradient from 0-50% EtOAc/Hexane) to yield Example 19D (106 mg, 77 % yield) as a colorless oil. MS (ESI) m/z: 450.3 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) d ppm 7.30 - 7.41 (5 H, m), 7.23 -7.28 (2 H, m), 6.76 (1 H, d, J=8.53 Hz), 5.03 (2 H, s), 4.67 (1 H, br. s.), 4.05 -4.12 (2 H, m), 3.39 (2 H, q, J=6.1 1 Hz), 2.81 (2 H, t, J=6.65 Hz), 0.89 - 0.95 (2 H, m), -0.02 - 0.03 (9 H, m).

Reference： [1]Patent: WO2014/201073,2014,A1 .Location in patent: Paragraph 00327

55
2-[5-bromo-2-(2,2-difluoro-ethoxy)-phenyl]-ethylamine [ No CAS ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl 5-bromo-2-(2,2-difluoroethoxy)phenylethyl(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine; In methanol;	Example 3 9C: 2-(Trimethylsilyl)ethyl 5-bromo-2-(2,2- difluoroethoxy)phenethyl(methyl)carbamate 1004301 Example 39B (0.486 g, 1.735 mmol) and 2-(trimethylsilyl)ethyl p-nitrophenyl carbonate (0.492 g, 1.735 mmol) were dissolved in MeOH (10.0 mL). DIPEA (0.909 mL, 5.21 mmol) was added, and the reaction was allowed to stir overnight. The reaction was concentrated in vacuo. The crude material was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to yield Example 39C (0.650 g, 75%)MS (ESI) m/z: 398.0 (M-28) (M-28 is consistent with Teoc containing compounds).1H NMR (400 MHz, CHLOROFORM-d) oe ppm 7.17 - 7.35 (2 H, m), 6.66 (1 H, d, J=8.53 Hz), 6.07 (1 H, tt, J=55.09, 4.02 Hz), 4.00 - 4.28 (4 H, m), 3.36 (2 H, q, J=6.53 Hz), 2.77(2 H, t, J=6.78 Hz), 0.87-0.98(2 H, m), -0.11 -0.11 (9 H, m).

Reference： [1]Patent: WO2014/201073,2014,A1 .Location in patent: Paragraph 00430

56
[ 1003-29-8 ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl 1H-pyrrole-2-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1001311 To a suspension of sodium hydride (164.0 mg, 4.10 mmol, 1.3 eq, 60% in mineral oil) in DMF (2.5 mL), 1H-2-pyrrole-carbaldehyde (300.0 mg, 3.15 mmol, 1.0 eq) was added at 0C, and the mixture was stirred at the same temperature for 20 minutes. A solution of 4-nitrophenyl-2- trimethylsilyl-ethyl carbonate (1.16 g, 4.10 mmol, 1.3 eq) in DMF (2.5 mL) was added, and the reaction temperature was left stirring at at 0C for 1 hour. Water (80 mL) was added to reaction mixture and extracted with EtOAc (80 mL). Organic layer was washed with H20 (2 x 80 mL), and then with brine (80 mL). Organic layer was separated, dried over Na2SO4, filtered, and concentrated under vacuum. Crude product (944.8 mg) was purified using Biotage SP purification system (10 g column, fraction size: 6 mL, weak eluant: n-hexane, strong eluant: n-hexane:EtOAc=6:1, elution of product at 5% of strong eluant) to afford N-2-(trimethylsilyl)ethyl-pyrrole-2-carbaldehyde was obtained. ?HNMR(DMSO-d6) : 10.18 (s, 1H), 7.59(m, 1H), 7.14 (m, 1H), 6.43 (m, 1H), 4.18-4.62 (m, 2H), 0.92-1.32 (m, 2H), 0.06 (s, 9H).
		To a suspension of sodium hydride (164.0 mg, 4.10 mmol, 1.3 eq, 60% in mineral oil) in DMF (2.5 mL), lH-2-pyrrole-carbaldehyde (300.0 mg, 3.15 mmol, 1.0 eq) was added at 0C, and the mixture was stirred at the same temperature for 20 minutes. A solution of 4-nitrophenyl-2- trimethylsilyl- ethyl carbonate (1.16 g, 4.10 mmol, 1.3 eq) in DMF (2.5 mL) was added, and the reaction temperature was left stirring at at 0C for 1 hour. Water (80 mL) was added to reaction mixture and extracted with EtOAc (80 mL). The organic layer was washed with H20 (2 x 80 mL), and then with brine (80 mL). The organic layer was separated, dried over Na2SO (, filtered, and concentrated under vacuum. Crude product (944.8 mg) was purified using Biotage SP purification system (10 g column, fraction size: 6 mL, weak eluant: n-hexane, strong eluant: -hexane:EtOAc=6: l, elution of product at 5% of strong eluant) to afford N-2-(trimethylsilyl)ethyl-pyrrole-2-carbaldehyde was obtained.lH NMR (DMSO-dg) delta: 10.18 (s, 1H), 7.59 (m, 1H), 7.14 (m, 1H), 6.43 (m, 1H), 4.18- 4.62 (m, 2H), 0.92-1.32 (m, 2H), 0.06 (s, 9H)
		To a suspension of sodium hydride (164.0 mg, 4.10 mmol, 1.3 eq, 60% in mineral oil) in DMF (2.5 mL), 1H-2-pyrrole-carbaldehyde (300.0 mg, 3.15 mmol, 1.0 eq) was added at 0 C., and the mixture was stirred at the same temperature for 20 minutes. A solution of 4-nitrophenyl-2-trimethylsilyl-ethyl carbonate (1.16 g, 4.10 mmol, 1.3 eq) in DMF (2.5 mL) was added, and the reaction temperature was left stirring at 0 C. for 1 hour. Water (80 mL) was added to reaction mixture and extracted with EtOAc (80 mL). The organic layer was washed with H2O (2*80 mL), and then with brine (80 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated under vacuum. Crude product (944.8 mg) was purified using Biotage SP purification system (10 g column, fraction size: 6 mL, weak eluant: n-hexane, strong eluant: n-hexane:EtOAc=6:1, elution of product at 5% of strong eluant) to afford N-2-(trimethylsilyl)ethyl-pyrrole-2-carbaldehyde was obtained. 1H NMR (DMSO-d6) delta: 10.18 (s, 1H), 7.59 (m, 1H), 7.14 (m, 1H), 6.43 (m, 1H), 4.18-4.62 (m, 2H), 0.92-1.32 (m, 2H), 0.06 (s, 9H).

Reference： [1]Patent: WO2015/28094,2015,A1 .Location in patent: Paragraph 00131
[2]Patent: WO2015/28095,2015,A1 .Location in patent: Paragraph 00180
[3]Patent: US2016/297830,2016,A1 .Location in patent: Paragraph 0250

57
[ 80149-80-0 ]
[ 159002-17-2 ]
(±)-2-(tert-butoxycarbonyl)amino-3-[2-(trimethylsilyl)-ethyloxycarbonyl]propionic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 7806 - 7819

58
[ 58635-45-3 ]
[ 80149-80-0 ]
C₁₈H₂₆N₂O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; at 22℃; for 13h;Inert atmosphere;	To a solution of 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (7.17 g, 25.3 mmol, 1.50 equiv) (Okoth, R.; Basu, A. Beilstein J. Org. Chem. 2013, 9, 608) in dichloromethane (170 mL) at 22 C. under an air atmosphere were sequentially added tryptamine methyl carbamate S4 (3.68 g, 16.9 mmol, 1 equiv), tetra-n-butylammonium hydrogen sulfate (570 mg, 1.69 mmol, 10.0 mol %), and powdered sodium hydroxide (2.02 g, 50.6 mmol, 3.00 equiv). After 13 h, the bright orange suspension was washed with an aqueous solution of sodium hydroxide (1N, 3*50 mL). The organic extract was dried over anhydrous sodium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 5%?20% ethyl acetate in hexanes) to afford tryptamine S5 (6.10 g, 99.6%) as white solid. Structural assignments were made using additional information from gCOSY, gHSQC, and gHMBC experiments. 1H NMR (400 MHz, CDCl3, 25 C.): delta 8.18 (d, J=7.5 Hz, 1H, C7H), 7.54 (d, J=7.6 Hz, 1H, C4H), 7.44 (s, 1H, C8aH), 7.34 (app-t, J=7.4 Hz, 1H, C6H), 7.25 (app-t, J=7.3 Hz, 1H, C5H), 4.76 (br-s, 1H, NH), 4.58-4.37 (m, 2H, C10H2), 3.66 (s, 3H, NHCO2CH3), 3.51 (dd, J=6.1, 12.4 Hz, 2H, C2H2), 2.91 (t, J=6.7 Hz, 2H, C3H2), 1.32-1.14 (m, 2H, C11H2), 0.11 (s, 9H, (C12H3)3). 13C NMR (100 MHz, CDCl3, 25 C.): delta 157.1 (NHCO2CH3), 151.1 (C9), 135.7 (C7a), 130.4 (C4a), 124.8 (C6), 122.9 (2C, C5, C8a) 119.0 (C4), 118.2 (C3a), 115.5 (C7), 65.7 (C10), 52.2 (NHCO2CH3), 40.6 (C2), 25.7 (C3), 17.9 (C11), 1.40 (C12). FTIR (thin film) cm-1: 3356 (m), 2955 (s), 1734 (s), 1526 (m), 936 (w). HRMS (DART) (m/z): calc'd for C18H27N2O4Si [M+H]+: 363.1735, found: 363.1758.10719] TEC (30% ethyl acetate in hexanes), Rf: 0.32 (UV CAM).10720] M.p.: 68-70 C. (CH2C12).

Reference： [1]Patent: US2019/119286,2019,A1 .Location in patent: Paragraph 0713; 0714; 0715; 0716; 0717; 0718-0720
[2]Journal of the American Chemical Society,2017,vol. 139,p. 17590 - 17596

59
(S)-4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzonitrile [ No CAS ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl (S)-(3-(4-cyanophenoxy)-3-(thiophen-2-yl)propyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.1 g	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	To a solution of the compound obtained in step a (3.0 g, 1 1.01 mmol) in DCM (25 mL), DIPEA (1 .92 mL, 1 1.01 mmol) and a solution of 4-nitrophenyl (2-(trimethylsilyl)ethyl)carbonate (3.12 g, 1 1 .01 mmol) in DCM (10 mL) were added and the reaction mixture was stirred at rt for 16 h. The reaction mixture was washed with NaHCC>3 sat solution and then with 2 M NaOH aq solution (three times). The organic layer was dried with Na2S04, the solvent was removed under vacuum and the residue was purified by flash chromatography, silica gel, gradient CH to 100% EtOAc, to afford the title compound (3.1 g, 66% global yield, 2 steps). HPLC-MS (Method B): Ret, 6.24 min; ESI+-MS m/z, 439.1 (M+Na).

Reference： [1]Patent: WO2017/191304,2017,A1 .Location in patent: Page/Page column 105

60
methyl (2-(7-azido-1H-indol-3-yl)ethyl)carbamate [ No CAS ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl-7-azido-3-(2-((methoxycarbonyl)amino)ethyl)-1H-indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.0%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; at 22℃; for 15.5h;	To a solution of methyl (2-(7-azido-lH-indol-3-yl)ethyl)carbamate (1.66 g, 6.40 mmol, 1 equiv), 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (2.72 g, 9.60 mmol, 1.50 equiv) and tetrabutylammonium hydrogensulfate (217 mg, 640 muiotatauiotaomicron, 10.0 mol%) in dichloromethane (64.0 mL) at 22 C was added finely powdered sodium hydroxide (768 mg, 19.2 mmol, 3.00 equiv). After 15.5 h, the reaction mixture was washed with aqueous sodium hydroxide (IN, 100 mL) and the aqueous layer was extracted with dichloromethane (3 x 50 mL). The combined organic layers were dried over anhydrous sodium sulfate, were filtered and were concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 5%- >15% acetone in hexanes) to afford 2- (trimethylsilyl)ethyl-7-azido-3-(2-((methoxycarbonyl)amino)ethyl)-lH-indole-l-carboxylate (2.53 g, 98.0%) as an off-white amorphous gum. Structural assignments were made using additional information from gHSQC and gHMBC experiments. NMR (400 MHz, CDCh, 20 C): delta 7.42 (s, 1H, C8aH), 7.35 (d, J = 7.7 Hz, 1H, C4H), 7.28 (app-t, J = 7.8 Hz, 1H, C5H), 7.14 (d, J = 8.4 Hz, 1H, CeH), 4.78 (br-s, 1H, NHCO2CH3), 4.544.44 (m, 2H, NC02CH2CH2Si(CH3)3), 3.67 (s, 3H, NHCO2CH3), 3.49 (dd, J = 6.4, 12.9 Hz, 2H, C2H2), 2.88 (t, J = 6.8 Hz, 2H, C3H2), 1.261.17 (m, 2H, NC02CH2CH2Si(CH3)3), 0.09 (s, 9H, NC02CH2CH2Si(CH3)3). 1 C NMR (100 MHz, CDCh, 20 C): delta 157.1 (NHCO2CH3), 150.4 (NC02CH2CH2Si(CH3)3), 133.9 (C4a), 127.9 (Cv), 126.8 (C7a), 126.1 (C8a), 124.1 (Cs), 117.8 (Csa), 116.0 (Ce), 115.9 (C4), 66.4 (NC02CH2CH2Si(CH3)3), 52.2 (NCO2CH3), 40.6 (C2), 25.6 (Cs), 17.7 (NC02CH2CH2Si(CH3)3), -1.4 (NC02CH2CH2Si(CH3)3). FTIR (thin film) cm 1: 3370 (m), 2954 (s), 2115 (s), 1728 (s), 1526 (w). HRMS (DART) (m/z): calculated for C18H29N6O4S1 [M+NH4]+: 421.2014, found 421.2005. TLC (20% ethyl acetate in hexanes), Rf: 0.34 (UV, CAM).
98.0%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; at 22℃; for 15.5h;Inert atmosphere;	To a solution of methyl (2-(7-azido-1H-indol-3-yl) ethyl)carbamate (1.66 g, 6.40 mmol, 1 equiv), 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (2.72 g, 9.60 mmol, 1.50 equiv) and tetrabutylammonium hydrogensulfate (217 mg, 640 tmol, 10.0 mol %) in dichloromethane (64.0 mE) at 22 C. was added finely powdered sodium hydroxide (768 mg, 19.2 mmol, 3.00 equiv). Afier 15.5 h, the reaction mixture was washed with aqueous sodium hydroxide (iN, 100 mE) and the aqueous layer was extracted with dichloromethane (3x50 mE). The combined organic layers were dried over anhydrous sodium sulfate, were filtered and were concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 5%- 15% acetone in hexanes) to afford 2-(trimeth- ylsilyl)ethyl-7-azido-3-(2-((methoxycarbonyl)amino)ethyl)- 1H-indole-1-carboxylate (2.53 g, 98.0%) as an off-white amorphous gum. Structural assignments were made using additional information from gHSQC and gHMI3C experiments.10600] ?H NMR (400 MHz, CDC13, 20 C.): oe 7.42 (s, 1H, C80H), 7.35 (d, J=7.7 Hz, 1H, C4H), 7.28 (app-t, J=7.8 Hz, 1H, C5H), 7.14 (d, J=8.4 Hz, 1H, C6H), 4.78 (br-s, 1H, NHCO2CH3), 4.54444 (m, 2H, NCO2CH2CH2Si(CH3)3), 3.67 (s, 3H, NHCO2CH3), 3.49 (dd, J=6.4, 12.9 Hz, 2H, C2H2), 2.88 (t, J=6.8 Hz, 2H, C3H2), 1.26117 (m, 2H, NCO2CH2CH2Si(CH3)3), 0.09 (s, 9H, NCO2CH2CH2Si (CH3)3).j0601] ?3C NMR (100 MHz, CDC13, 20 C.): oe 157.1 (NHCO2CH3), 150.4 (NCO2CH2CH2Si(CH3)3), 133.9 (C4j, 127.9 (C7), 126.8 (C70), 126.1 (C80), 124.1 (C5), 117.8 (C3j, 116.0 (C5), 115.9 (C4), 66.4 (NCO2CH2CH2Si (CH3)3), 52.2 (NCO2CH3), 40.6 (C2), 25.6 (C3), 17.7 (NCO2CH2CH2Si(CH3)3), -1.4 (NCO2CH2CH2Si(CH3)3). 10602] FTIR (thin film) cm?: 3370 (m), 2954 (s), 2115 (s), 1728 (s), 1526 (w).j0603] HRMS (DART) (mlz): calculated for C, 8H29N6O4Si [M+NH4]: 421.2014, found 421.2005.10604] TEC (20% ethyl acetate in hexanes), Rf: 0.34 (UV CAM).

Reference： [1]Patent: WO2017/205539,2017,A1 .Location in patent: Paragraph 00224-00229
[2]Patent: US2019/119286,2019,A1 .Location in patent: Paragraph 0508; 0591; 0598-0604

61
[ 80149-80-0 ]
[ 197006-11-4 ]
C₁₄H₂₇NO₃Si [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4475 - 4477

62
[ 80149-80-0 ]
[ 35761-26-3 ]
(2S)-2-(benzyloxycarbonylamino)-3-(2-trimethylsilylethoxycarbonylamino)propanoic acid [ No CAS ]

Reference： [1]Patent: WO2018/149419,2018,A1 .Location in patent: Paragraph 001255; 001256

63
[ 80149-80-0 ]
[ 109055-42-7 ]
[ 401601-05-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine In dichloromethane at 20℃;

Reference： [1]Nørager, Niels G.; Poulsen, Mette H.; Strømgaard, Kristian [Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 8048 - 8053]

64
[ 40377-41-1 ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl (4-(2-acetamidoethyl)phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;	To a stirred solution of N-(4-aminophenethyl)acetamide (200 mg, 1.12 mmol, 1 eq) and TEA (in DCM (10 ml) at 0 C., is added 4-nitrophenyl 2-(trimethylsilyl)ethyl carbonate (286 mg, 1.01 mmol) over a period of 5 minutes. The reaction mixture is stirred at room temperature overnight, diluted with DCM (10 ml), washed with a saturated aqueous solution of NaHSO4 (5 ml), a saturated solution of NaHCO3 (aq) (5 ml), water (3*5 ml), dried over MgSO4 and concentrated to dryness to afford the title compound as a white solid.

Reference： [1]Patent: US2019/10113,2019,A1 .Location in patent: Paragraph 0101; 0102; 0103

65
3-(3-iodophenoxy)-N-methyl-3-(thiophen-2-yl)propan-1-amine [ No CAS ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl (3-(3-iodophenoxy)-3-(thiophen-2-yl)propyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	Step 3: Title compound. (0345) To a solution of the compound obtained in step 2 (500 mg, 1 .34 mmol) in DCM (15 mL), DIPEA (233 mL, 1.34 mmol) and 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (380 mg, 1.34 mmol) in DCM (5 mL) were added. The reaction mixture was stirred at r.t. for 16 h. Sat. aqueous NaHCC>3 solution was added to the mixture and the product extracted with DCM. The combined organic fractions were washed with 10% NaOH (3x) and dried over MgS04. After filtration, the solvent was removed under reduced pressure to give a residue which was purified by combiflash chromatography (S1O2, CH/EtOAc up to 100%) to give the title compound (452 mg, 65% yield) as oil. (0346) HPLC ret time (method A): 2.97 min; ESI- MS: m/z 516.2 [M-H]

Reference： [1]Patent: WO2019/2173,2019,A1 .Location in patent: Page/Page column 61

66
(S)-3-(3-bromophenoxy)-N-methyl-3-(thiophen-2-yl)propan-1-amine [ No CAS ]
[ 80149-80-0 ]
(S)-2-(trimethylsilyl)ethyl (3-(3-bromophenoxy)-3-(thiophen-2-yl)propyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 16h;	Step 2. Title compound. (0351) To a solution of the compound obtained in step 1 (369 mg, 1 .13 mmol) in DCM (10 mL), DIPEA (197 mu, 1 .13 mmol) was added, followed by the dropwise addition of 4- nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (320 mg, 1.31 mmol) in DCM (2 mL). The reaction mixture was stirred for 16 h. Sat. aqueous NaHCC>3 solution was added to the mixture and the product extracted with DCM. The combined organic fractions were washed with 10% NaOH, dried over MgS04, filtered and the solvent removed under reduced pressure to give the title compound (481 mg, 90% yield. (0352) HPLC ret time (method A): 2.89 min; ESI- MS: m/z 468.1 [M+H]

Reference： [1]Patent: WO2019/2173,2019,A1 .Location in patent: Page/Page column 62

67
(R)-3-(3-bromophenoxy)-N-methyl-3-(thiophen-2-yl)propan-1-amine [ No CAS ]
[ 80149-80-0 ]
(R)-2-(trimethylsilyl)ethyl (3-(3-bromophenoxy)-3-(thiophen-2-yl)propyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 16h;	Step 4: Title compound. (0360) To a solution of the compound obtained in step 3 (1 .36 g, 4.17 mmol) in DCM (15 mL), DIPEA (726 mu, 4.17 mmol) was added followed by the dropwise addition of 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (1.18 g, 4.17 mmol) in DCM (5 mL). The reaction mixture was stirred for 16 h. Sat. aqueous NaHCOs solution was added to the mixture and the product extracted with DCM. The combined organic fractions were washed with 10% NaOH, dried over MgS04 and filtered. The solvent was removed under reduced pressure to give the title compound (1 .78 g, 91 % yield). (0361) HPLC ret time (method A): 2.96 min; ESI- MS: m/z 468.4 [M-H]"

Reference： [1]Patent: WO2019/2173,2019,A1 .Location in patent: Page/Page column 63

68
4-iodobenzamidine [ No CAS ]
[ 80149-80-0 ]
C₁₃H₁₉IN₂O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.8 g	With potassium carbonate; In tetrahydrofuran; water; at 20℃; for 3h;	4-iodobenzoquinone 3.2 g and Teoc-ONP 4.9 g were weighed, placed in a 250 mL one-mouth reaction flask, and 100 mL of tetrahydrofuran was added.20 mL of an aqueous solution of 4.4 g of potassium carbonate was slowly added dropwise, and the reaction was stirred at room temperature for 3 hours. The reaction solution is slowly poured into saturated carbonic acidAn aqueous solution of sodium hydrogen carbonate (300 mL) was added three times with ethyl acetate, and the ethyl acetate phase obtained by three-time liquid separation was used.Wash with brine and dry over anhydrous sodium sulfate. After filtering, the filtrate was concentrated.The column was subjected to Teoc-4-iodobenzoquinone 4.8 g.

Reference： [1]Patent: CN109369698,2019,A .Location in patent: Paragraph 0007

69
(S)-3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzonitrile [ No CAS ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl (S)-(3-(3-cyanophenoxy)-3-(thiophen-2-yl)propyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
600 mg	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	To a solution of the compound obtained in step a) (500 mg, 1.84 mmol) in DCM (6 mL), DIPEA (0.32 mL, 1 .84 mmol) and a solution of 4-nitrophenyl (2- (trimethylsilyl)ethyl)carbonate (520 mg, 1.84 mmol) in DCM (6 mL) were added and the reaction mixture was stirred at rt for 16 h. The reaction mixture was washed with NaHCC>3 sat solution and then with 2 M NaOH aq solution (three times). The organic layer was dried with Na2S04, the solvent was removed under vacuum and the residue was purified by flash chromatography, silica gel, gradient CH to 100% EtOAc, to afford the title compound (600 mg, 78% global yield, 2 steps). HPLC-MS (Method B): Ret, 6.29 min; ESr-MS m/z, 439.1.

Reference： [1]Patent: WO2019/77106,2019,A1 .Location in patent: Page/Page column 47

70
N-ethylglycine trifluoroacetate salt [ No CAS ]
[ 80149-80-0 ]
N-ethyl-N-((2-(trimethylsilyl)ethoxy)carbonyl)glycine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 64h;	To a solution of N-ethylglycine trifluoroacetate salt (646 mg, 2.27 mmol) in DCM (5 mL), DIPEA (1.1 mL, 6.30mmol) and a solution of 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (900 mg, 3.18mmol) in DCM (5 mL) were added and the mixture was stirred at rt for 64 h. NaHCO3 satsolution was added and washed with DCM. The aq layerwas treated with HCI 1 N solution until pH<4 and extracted with DCM. The organic layer was dried with Na2SO4, filtered and concentrated under vacuum. Purification by flash chromatography, silica gel, gradient DCM to 30% MeOH afforded the title compound (542 mg, 69% yield).1H-NMR (400 MHz, ODd3), ppm: 7.96 (bs, 1H), 4.22 (m, 2H), 4.02 (m, 2H), 3.39 (m,2H), 1.12 (t, J=7.3 Hz, 3H), 1.04 (m, 2H), 0.06 (s, 9H).

Reference： [1]Patent: WO2019/81691,2019,A1 .Location in patent: Page/Page column 75

71
methyl (S)-4-(3-((tert-butoxycarbonyl)(methyl)amino)-1-(thiophen-2-yl)propoxy)-2-methylbenzoate [ No CAS ]
[ 80149-80-0 ]
methyl (S)-2-methyl-4-(3-(methyl((2-(trimethylsilyl)ethoxy)carbonyl)amino)-1-(thiophen-2-yl)propoxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		In a round-bottom flask, Zn Br2 (5.5 g, 24.67 mmol)was dried under vacuum at 200 O for 4 h. Once the solid reached rt, a solution of thecompound obtained in step a (2.07 g, 4.93 mmol) in DOM (49 mL) was added and themixture was stirred at rt under Ar atmosphere for 20 h. Water was added and the mixture was stirred for 2 h. The layers were decanted, the aq layer was extracted with DOM and the organic layer was concentrated under vacuum. The residue was dissolved in DOM (8.5 mL), DIPEA (2.6 mL, 15.15 mmol) and a solution of 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (1 .6 g, 5.55 mmol) in DOM (8.5 mL) were added and the mixture was stirred at rt for 16 h. The reaction mixture was concentrated under vacuum. Purification by flash chromatography, silica gel, gradient OH to 100% EtOAc afforded the title compound (1.1 g, 47% yield). HPLC (Method B): Ret, 7.18 mm; ESl-MS m/z, 486.1 (M+Na).

Reference： [1]Patent: WO2019/81691,2019,A1 .Location in patent: Page/Page column 76

72
(R)-3-(2-bromophenoxy)-N-ethyl-3-(thiophen-2-yl)propan-1-amine [ No CAS ]
[ 80149-80-0 ]
(R)-2-(trimethylsilyl)ethyl (3-(2-bromophenoxy)-3-(thiophen-2- yl)propyl)(ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine; In dichloromethane;	To a solution of the product obtained in Step 2 (1.14 g, 3.3 mmol) in DCM (1.5 ml_), under a N2 atmosphere, DIPEA (0.58 ml_, 3.3 mml) and a solution of 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (0.95 g, 3.3 mmol) in DCM (1.5 mL) were added. After stirring at r.t. overnight, NaHCOs sat. solution was added and it was extracted twice with DCM. The combined organic phases were washed with 2 N NaOH solution, dried over MgS04, filtered and concentrated to dryness. The residue was purified by flash chromatography, silica gel, gradient CH to EtOAc to give the title compound (1.46 g, 90% yield).
90%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere;	To a solution of the product obtained in Step 2 (1.14 g, 3.3 mmol) in DCM (1.5 mL), under a N2 atmosphere, DIPEA (0.58 mL, 3.3 mmol) and a solution of 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (0.95 g, 3.3 mmol) in DCM (1.5 mL) were added and the mixture was stirred at r.t. overnight. NaHCOs sat. solution was added and it was extracted twice with DCM. The combined organic phases were washed with 2 N NaOH solution, dried over MgS04, filtered and concentrated to dryness. The residue was purified by flash chromatography, silica gel, gradient CH to EtOAc, to give the title compound (1 .46 g, 90% yield).
90%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere;	To a solution of the product obtained in Step 2 (1.14 g, 3.3 mmol) in DCM (1.5 mL), DIPEA (0.58 mL, 3.3 mmol) and a solution of 4-nitrophenyl (2- (trimethylsilyl)ethyl) carbonate (0.95 g, 3.3 mmol) in DCM (1.5 mL) were added under a N2 atmosphere and the mixture was stirred at r.t. overnight. NaHCO3 sat. solution was added and it was extracted twice with DCM. The combined organic phases were washed with 2 N NaOH aq. solution, dried over MgSO4, filtered and concentrated to dryness. The residue was purified by flash chromatography, silica gel, gradient CH to EtOAc, to give the title compound (1.46 g, 90% yield).

90%

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere;

Title compound: To a solution of the product obtained in Step 2 (1.14 g, 3.3 mmol) in DCM (1.5 ml_), DIPEA (0.58 ml_, 3.3 mmol) and a solution of 4-nitrophenyl (2- (trimethylsilyl)ethyl) carbonate (0.95 g, 3.3 mmol) in DCM (1.5 mL) were added under a N2 atmosphere and the mixture was stirred at r.t. overnight. NaHCC>3 sat. solution was added and it was extracted twice with DCM. The combined organic phases were washed with 2 N NaOH aq. solution, dried over MgS04, filtered and concentrated to dryness. The residue was purified by flash chromatography, silica gel, gradient CH to EtOAc, to give the title compound (1.46 g, 90% yield).

Reference： [1]Patent: WO2019/110137,2019,A1 .Location in patent: Page/Page column 238; 239
[2]Patent: WO2019/115008,2019,A1 .Location in patent: Page/Page column 319; 320
[3]Patent: WO2019/149919,2019,A1 .Location in patent: Page/Page column 325; 326
[4]Patent: WO2019/180188,2019,A1 .Location in patent: Page/Page column 330

73
(R)-3-(2-bromophenoxy)-N-methyl-3-(thiophen-2-yl)propan-1-amine [ No CAS ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl N-[(3R)-3-(2-bromophenoxy)-3-(thiophen-2-yl)propyl]-N-methylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere;	To a solution of the product obtained in Step 2 (1.67 g, 5.1 mmol) in DCM (5 ml_), under a N2 atmosphere, DIPEA (0.89 ml_, 5.1 mmol) and a solution of 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (1.45 g, 5.1 mmol) in DCM (7 ml.) were added and the mixture was stirred at r.t. overnight. NaHCC>3 sat. solution was added and it was extracted twice with DCM. The combined organic phases were washed with 2 N NaOH solution, dried over MgS04, filtered and concentrated to dryness. The residue was purified by flash chromatography, silica gel, gradient CH to EtOAc, to give the title compound (2.17 g, 91% yield).
91%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere;	Step 3. Title compound: To a solution of the product obtained in Step 2 (1.67 g, 5.1mmol) in DCM (5 mL), under a N2 atmosphere, DIPEA (0.89 mL, 5.1 mmol) and asolution of 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (1.45 g, 5.1 mmol) in DCM(7 mL) were added and the mixture was stirred at r.t. overnight. NaHCO3 sat. sol. wasadded and it was extracted twice with DCM. The combined organic phases werewashed with 2 N NaOH solution, dried over Mg504, filtered and concentrated todryness. The residue was purified by flash chromatography, silica gel, gradient OH toEtOAc, to give the title compound (2.17 g, 91% yield).

Reference： [1]Patent: WO2019/180189,2019,A1 .Location in patent: Page/Page column 288-289
[2]Patent: WO2020/21021,2020,A1 .Location in patent: Page/Page column 190-191

74
[ 282551-10-4 ]
[ 80149-80-0 ]
2-(trimethylsilyl)ethyl (2-(2-(2-hydroxyethoxy)ethoxy)ethyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a stirred solution of 2-(2-(2-(methylamino)ethoxy)ethoxy)ethan-l-ol (1.8 g, 0.005 mol) and triethylamine (1.01 g, 0.01 mol) in dichloromethane (30 mL), was added 4-nitrophenyl (2-(trimethylsilyl)ethyl) carbonate (3.1 g, 0.02 mol) at 0C.The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (20 mL), washed with water and brine (30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford a crude residue which was purified by silica gel flash chromatography (eluted with 20-30% ethyl acetate in hexane) to afford 2-(trimethylsilyl)ethyl (2-(2-(2-hydroxyethoxy)ethoxy)ethyl)(methyl)carbamate (560 mg, 42%) as colorless oil.

Reference： [1]Patent: WO2019/195609,2019,A2 .Location in patent: Paragraph 001056-001057

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	80149-80-0	MDL No. :	MFCD00042930
Formula :	C₁₂H₁₇NO₅Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZAQWGGKIMQIVGM-UHFFFAOYSA-N
M.W :	283.35	Pubchem ID :	3086116
Synonyms :

Num. heavy atoms :	19
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	7
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	75.33
TPSA :	81.35 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.12 cm/s

Log Po/w (iLOGP) :	2.65
Log Po/w (XLOGP3) :	4.1
Log Po/w (WLOGP) :	3.45
Log Po/w (MLOGP) :	1.63
Log Po/w (SILICOS-IT) :	-0.85
Consensus Log Po/w :	2.2

[ CAS No. 80149-80-0 ] {[proInfo.proName]}

Quality Control of [ 80149-80-0 ]

Related Doc. of [ 80149-80-0 ]

Product Details of [ 80149-80-0 ]

Calculated chemistry of [ 80149-80-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 80149-80-0 ]

Application In Synthesis of [ 80149-80-0 ]

[ 80149-80-0 ] Synthesis Path-Upstream 1~4

[ 80149-80-0 ] Synthesis Path-Downstream 1~74

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.95
Solubility :	0.0317 mg/ml ; 0.000112 mol/l
Class :	Soluble
Log S (Ali) :	-5.51
Solubility :	0.000867 mg/ml ; 0.00000306 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.28
Solubility :	0.149 mg/ml ; 0.000526 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	4.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.93

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P263	Avoid contact during pregnancy/while nursing.
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P270	Do not eat, drink or smoke when using this product.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
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P313	Get medical advice/attention.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
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P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
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P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling