[ CAS No. 77087-60-6 ] {[proInfo.proName]}

Name: 77087-60-6|(S)-Methyl 2-amino-3-((tert-butoxycarbonyl)amino)propanoate|96%
Brand: Ambeed
SKU: A126936
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Quality Control of [ 77087-60-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 77087-60-6 ]

CAS No. :	77087-60-6	MDL No. :	MFCD04039602
Formula :	C₉H₁₈N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AXLHVTKGDPVANO-LURJTMIESA-N
M.W :	218.25	Pubchem ID :	7021143
Synonyms :

Safety of [ 77087-60-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 77087-60-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 77087-60-6 ]
Downstream synthetic route of [ 77087-60-6 ]

[ 77087-60-6 ] Synthesis Path-Upstream 1~10

1
[ 58457-98-0 ]
[ 77087-60-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 567 - 572
[2] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 3, p. 339 - 344
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 13, p. 2409 - 2421
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 31, p. 7015 - 7022
[5] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 12, p. 1415 - 1420
[6] Synthesis, 1989, # 7, p. 542 - 544
[7] Patent: US2012/178773, 2012, A1, . Location in patent: Page/Page column 26

2
[ 24424-99-5 ]
[ 6059-44-5 ]
[ 77087-60-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With triethylamine In dichloromethane at -78℃; for 2 h; Inert atmosphere; Cooling with ice	An amount of 10.0 g (0.053 mol) of compound 1 was suspended in 1 L of CH₂CI₂and kept in presence of argon at -78°C. Triethylamine (30 ml, 0.20 mol) was added dropwise to the cold suspension to obtain a solution mixture. Di-r-butyldicarbonate (11.6 g, 0.054 mol) was dissolved in 100 mL CH₂CI₂and added dropwise to the mixture. After the addition was completed the reaction was placed in an ice bath and stirred for 2h. The reaction was transferred to a separation funnel and extracted with 2 x 50 mL of 10percent Na₂S0₄solution. After the aqueous layer was washed with 3 x 10 mL CH₂CI₂, the pH was adjusted to 10 using saturated NaHC0₃and 3N NaOH solutions, it was extracted with 10 x 100 mL of CH₂CI₂. The organic layer was dried over MgS0_4;filtered and concentrated to obtain 4.9 g of a pale yellow oil. Column chromatography on silica gel in 2.5percentMeOH/ EtOAc resulted 4.32g of the product (53percent).HRMS: 219.1324 (M+H⁺), 241.11436 (M+Na⁺).*H NMR (300 MHz, CDCI₃): 6[ppm]= 5.11 (s, 1H), 3.78 - 3.69 (s, 3H), 3.60 - 3.46 (m, 2H), 3.31- 3.15 (m, 1H), 1.64 (s, 2H),1.42 (s, 9H).1³C MR (75 MHz, CDCI₃):5[ppm]= 174.46, 155.94, 79.48, 54.36, 52.26, 44.16, 28.30.

Reference： [1] Patent: WO2014/122228, 2014, A1, . Location in patent: Page/Page column 23; 24
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 23, p. 9971 - 9982

3
[ 24424-99-5 ]
[ 77087-60-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 13, p. 2409 - 2421
[2] Patent: US5786373, 1998, A,

4
[ 16947-84-5 ]
[ 77087-60-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 567 - 572
[2] Patent: US2012/178773, 2012, A1,

5
[ 24424-99-5 ]
[ 6059-44-5 ]
[ 61040-20-8 ]
[ 77087-60-6 ]

Reference： [1] Synthetic Communications, 1993, vol. 23, # 5, p. 703 - 709

6
[ 1070-19-5 ]
[ 77087-60-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 567 - 572

7
[ 16947-86-7 ]
[ 77087-60-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 567 - 572

8
[ 74536-29-1 ]
[ 77087-60-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 567 - 572

9
[ 126046-25-1 ]
[ 77087-60-6 ]

Reference： [1] Synthesis, 1989, # 7, p. 542 - 544

10
[ 162558-25-0 ]
[ 77087-60-6 ]

Reference： [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3153 - 3157

[ 77087-60-6 ] Synthesis Path-Downstream 1~70

1
[ 24424-99-5 ]
[ 6059-44-5 ]
[ 61040-20-8 ]
[ 77087-60-6 ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 703 - 709

2
[ 39637-99-5 ]
[ 77087-60-6 ]
[ 126046-29-5 ]

Reference： [1]Synthesis,1989,p. 542 - 544

3
[ 58457-98-0 ]
[ 77087-60-6 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; hydrogen;5%-palladium/activated carbon; In water; under 3620.13 Torr; for 2h;	Preparation of Compound CCA solution of Compound BB (29.6 g, 83.8 mmol) in MeOH (500 mL) was treated with palladium (5 wt. % on activated carbon, 100 mg) suspended in water (5 mL), and subjected to hydrogenation at 70 psi for 2 h. The reaction mixture was then filtered using a celite pad, and the removal of MeOH in vacuo yielded Compound CC, yield exceeded quantitative, (18.5 g, 83.8 mmol) as a colorless oil. LC-MS [M+H] 219.0 (C9H18N2O4+H, calc: 219.3). Compound CC was used directly in the next reaction without further purification.

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 339 - 344
[3]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421
[4]European Journal of Organic Chemistry,2014,vol. 2014,p. 7015 - 7022
[5]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1415 - 1420
[6]Synthesis,1989,p. 542 - 544
[7]Patent: US2012/178773,2012,A1 .Location in patent: Page/Page column 26

4
[ 20445-33-4 ]
[ 77087-60-6 ]
[ 126046-28-4 ]

Reference： [1]Synthesis,1989,p. 542 - 544

5
[ 501-53-1 ]
[ 77087-60-6 ]
[ 58457-98-0 ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 703 - 709

6
[ 77087-62-8 ]
[ 77087-60-6 ]
[ 77087-64-0 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572

7
[ 605-65-2 ]
[ 77087-60-6 ]
[ 178982-77-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1415 - 1420

8
[ 77087-60-6 ]
[ 592-34-7 ]
[ 169605-34-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 339 - 344

9
[ 77087-60-6 ]
[ 98-59-9 ]
[ 169604-92-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 339 - 344

10
[ 103-71-9 ]
[ 77087-60-6 ]
(S)-3-tert-Butoxycarbonylamino-2-(3-phenyl-ureido)-propionic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2064 - 2084

11
[ 80466-79-1 ]
[ 77087-60-6 ]
[ 185536-65-6 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1178 - 1192

12
[ 26118-68-3 ]
[ 77087-60-6 ]
C₁₃H₂₇N₃O₆S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1178 - 1192

13
[ 1899-93-0 ]
[ 77087-60-6 ]
[ 197092-14-1 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1178 - 1192

14
[ 2905-25-1 ]
[ 77087-60-6 ]
[ 1026810-59-2 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1178 - 1192

15
[ 77087-60-6 ]
[ 98-09-9 ]
[ 156185-58-9 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1178 - 1192
[2]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

16
[ 77087-60-6 ]
[ 133-59-5 ]
[ 197092-16-3 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1178 - 1192

17
[ 16133-25-8 ]
[ 77087-60-6 ]
[ 168157-14-0 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

18
[ 16629-19-9 ]
[ 77087-60-6 ]
[ 168157-15-1 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

19
[ 2386-60-9 ]
[ 77087-60-6 ]
[ 156185-57-8 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

20
[ 69371-75-1 ]
[ 77087-60-6 ]
[ 168157-11-7 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

21
[ 124-63-0 ]
[ 77087-60-6 ]
[ 1027972-04-8 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

22
[ 98-60-2 ]
[ 77087-60-6 ]
[ 1026158-73-5 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

23
[ 24424-99-5 ]
[ 77087-60-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol; dichloromethane; ethyl acetate;	Methyl [2(S)-Amino-3-(N-t-Butyloxycarbonylamino)]propionate (2-13) 2-12 (6.0 g, 31.5 mmol) was crushed to a fine powder, suspended in 1 L of CH2 Cl2 and cooled to -78 C. under argon. Triethylamine (17.5 mL, 0.126 mol, 4 eq) was added dropwise as the solution gradually became homogeneous. Di-t-butyldicarbonate (6.18 g, 2.83 mmol, 0.9 eq) was dissolved in 50 mL CH2 Cl2 and added dropwise to the solution. After the addition was completed, the reaction was placed in an ice bath and stirred for 1 1/2 hours. The reaction was transferred to a separatory funnel and extracted with 350 mL of 10% KHSO4 solution. The aqueous layer was washed with 310 mL of CH2 Cl2, than basified with saturated NaHCO3 and 3N NaOH solution to pH10 and extracted with 10*100 mL of CH2 Cl2. The organic layer was dried with Na2 SO4, filtered and evaporated to give 4.9 g of a pale yellow oil. Column chromatography in 2.5% MeOH/EtOAc gave 2-13 as an oil. Rf 0.39 (5% MeOH/EtOAc). 1 H NMR (400 MHz, CDCl3) delta 5.0 (bs, 1H), 3.72 (s, 3H), 3.56 (t, J=5.7 Hz, 1H), 3.46 (m, 1H), 3.23 (m, 1H), 1.55 (bs, 2H), 1.42 (s, 9H).

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421
[2]Patent: US5786373,1998,A

24
(S)-4-Isocyanatomethyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester [ No CAS ]
[ 77087-60-6 ]

Reference： [1]Synthesis,1989,p. 542 - 544

25
[ 126046-25-1 ]
[ 77087-60-6 ]

Reference： [1]Synthesis,1989,p. 542 - 544

26
[ 1070-19-5 ]
[ 77087-60-6 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572

27
[ 16947-84-5 ]
[ 77087-60-6 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572
[2]Patent: US2012/178773,2012,A1

28
[ 16947-86-7 ]
[ 77087-60-6 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572

29
[ 74536-29-1 ]
[ 77087-60-6 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572

30
[ 77087-60-6 ]
[ 77100-18-6 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572

31
[ 77087-60-6 ]
(S)-2-({(R)-1-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572

32
[ 77087-60-6 ]
[ 77087-66-2 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572

33
[ 77087-60-6 ]
[ 77087-65-1 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 567 - 572

34
[ 77087-60-6 ]
[ 91702-98-6 ]
2-(2-Acetylsulfanylmethyl-3-phenylpropionylamino)-3-tert-butoxycarbonylamino-propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	N-3-(tert-Butoxycarbonylamino)-L-alanine methyl ester (167 mg, 0.76 mmol) and 2-Acetylsulfanylmethyl-3-phenylpropionic acid (181 mg, 0.76 mmol) were dissolved in dichloromethane (2 ml). Then N-methylmorpholine (0.25 ml, 2.3 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (174 mg, 0.9 mmol) and hydroxybenzotriazole (135 mg, 1 mmol) were added and the reaction mixture stirred at rt over night. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography (silica gel, ethyl acetate/hexanes). MS-(M-H+) 439.6

Reference： [1]Patent: US2006/46978,2006,A1 .Location in patent: Page/Page column 14

Yield	Reaction Conditions	Operation in experiment
		Methyl 2(S)-Amino-3-(N-t-butyloxycarbonyl)aminopropionate (23-4) To a solution of 6.60 g (0.0187 mol) 23-3 in 150 ml EtOH was added 0.5 g of 10% Pd/C. The resulting mixture was hydrogenated under balloon pressure at r.t. for 4 hrs. The catalyst was filtered off and the solvent removed in vacuo to provide 23-4 as a viscous oil. 1 H NMR (300 MHz, CDCl3) delta 1.45 (9H, s), 1.49 (2H, m), 1.59 (2H, m), 3.25 (1H, m), 3.49 (1H, m), 3.58 (1H,m), 3.75 (3H, s), 5.03 (1H, m).
		Methyl 2-(S)-amino-3-(N-t-butyloxycarbonyl)aminoproprionate (5-4) To a solution of 6.60 g (0.0187 mol) 5-3 in 150 ml EtOH was added 0.5 g of 10% Pd/C. The resulting mixture was hydrogenated under balloon pressure at r.t. for 4 hrs. The catalyst was filtered off and the solvent removed in vacuo to provide 5-4 as a viscous oil. 1 H NMR (300 MHz, CDCl3) delta 1.45 (9H, s), 1.49 (2H, m), 1.59 (2H, m), 3.25 (1H, m), 3.49 (1H, m), 3.58 (1H, m), 3.75 (3H, s), 5.03 (1H, m).
		Methyl 2(S)-amino-3-(N-t-butyloxycarbonyl)aminopropionate (5-4) To a solution of 6.60 g (0.0187 mol) 5-3 in 150 ml EtOH was added 0.5 g of 10% Pd/C. The resulting mixture was hydrogenated under balloon pressure at r.t. for 4 hrs. The catalyst was filtered off and the solvent removed in vacuo to provide 5-4 as a viscous oil. 1 H NMR (300 MHz, CDCl3) delta1.45 (9H, s), 1.49 (2H, m), 1.59 (2H, m), 3.25 (1H, m), 3.49 (1H, m), 3.58 (1H,m), 3.75 (3H, s), 5.03 (1H, m)

36
[ 2386-60-9 ]
[ 77087-60-6 ]
Methyl 2-(S)-butylsulfonylamino-3-(N-t-butylcarbonyl)aminopropionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In water; acetonitrile;	Methyl 2(S)-Butylsulfonylamino-3-(N-t-butylcarbonyl)aminopropionate (23-5) To a solution of 0.400 g (0.00183 mol) of 23-4 in 10 ml of CH3 CN was added 0.226 g (0.00286 mol) pyridine followed by 0.408 g (0.0026 mol) of n-butanesulfonyl chloride. The resulting solution was stirred at room temperature for 2.5 hrs at which time starting material was consumed. The solvent was removed in vacuo and 50 ml of H2 O added to the residual material. This mixture was extracted with 3*50 ml portions of ethyl acetate and the combined extracts layer was dried (Na2 SO4), filtered and concentrated to give 0.5 g of a viscous oil.
	With pyridine; In water; acetonitrile;	Methyl 2-(S)-butylsulfonylamino-3-(N-t-butylcarbonyl)aminopropionate (5-5) To a solution of 0.400 g (0.00183 mol) of 5-4 in 10 ml of CH3 CN was added 0.226 g (0.00286 mol) pyridine followed by 0.408 g (0.0026 mol) of n-butanesulfonyl chloride. The solution was stirred at room temperature for 2.5 hrs at which time starting material was consumed. The solvent was removed in vacuo and 50 ml of H2 O added to the residual material. This mixture was extracted with 3*50 ml portions of ethyl acetate and the combined extracts layer was dried (Na2 SO4) filtered and concentrated to give 0.5 g of viscous oil.
	With pyridine; In water; acetonitrile;	Methyl 2(S)-butylsulfonylamino-3-(N-t-butylcarbonyl)aminopropionate (5-5) To a solution of 0.400 g (0.00183 mol) of 5-4 in 10 ml of CH3 CN was added 0.226 g (0.00286 mol) pyridine followed by 0.408 g (0.0026 mol) of n-butanesulfonyl chloride. The resulting solution was stirred at room temperature for 2.5 hrs at which time starting material was consumed. The solvent was removed in vacuo and 50 ml of H2 O added to the residual material. This mixture was extracted with 3*50 ml portions of ethyl acetate and the combined extracts washed with brine, dried (Na2 SO4), filtered and concentrated to give 0.5 g of a viscous oil.

Reference： [1]Patent: US5416099,1995,A
[2]Patent: US5525617,1996,A
[3]Patent: US5559127,1996,A

37
[ 77087-60-6 ]
[ 3173-56-6 ]
2(S)-Benzylureido-3-(N-t-butyloxycarbonyl)aminopropionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	2(S)-Benzylureido-3-(N-t-butyloxycarbonyl)aminopropionic acid methyl ester (5-9) A solution of 5-4 (1.29 g, 5.9 mmoles) in THF (35 ml) was treated with benzylisocyanate (6.5 mmoles) at room temperature. After stirring for 16 hours, the solvent was removed and the residue was purified by flash chromatography on silica gel eluding with 5% MeOH/EtOAc to give 5-9. Rf 0.7 (silica, 10% MeOH/EtOAc) 1 H NMR (300 MHz, CD3 OD) delta1.45 (9H, s), 3.41 (1H, m), 3.53 (1H, m), 3.62 (3H, s), 3.70 (1H, s), 4.32 (3H, m), 5.27 (1H, m), 5.45 (1H, m), 5.90 (1H, m).

Reference： [1]Patent: US5559127,1996,A

38
[ 77087-60-6 ]
[ 3218-36-8 ]
[ 702690-91-3 ]

Yield	Reaction Conditions	Operation in experiment
80%		General Procedure (E): Ester Method Step A: To w-N-protected amino acid methyl ester hydrochloride (10 mmol) and aldehyde (10.3 mmol) in THF (80 ml) is added at room temperature sodium triacetoxyborohydride (11 mmol) and the mixture is stirred overnight. Sat. aq. potassium carbonate (100 ml) is added and the mixture is stirred for 1 h. The layers are separated and the aq. layer is extracted with ethyl acetate (3×100 ml). The combined org. layers are dried over sodium sulfate and evaporated in vacuo. Flash chromatography (silica, dichloromethane) afforded the product.

Reference： [1]Patent: US2007/185128,2007,A1 .Location in patent: Page/Page column 13

39
[ 728878-27-1 ]
[ 77087-60-6 ]
[ 728878-14-6 ]

Yield	Reaction Conditions	Operation in experiment
91%		DIEA (10.5ml, 60.3mmol) was added to a stirred solution of 4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-benzoicacid (1) (5.0g, 19.1mmol), HOBT (2.72g, 20.1mmol), EDC (3.85g, 20.1mmol) in DMF (80ml). After 2 min., the HDAP(Boc)-OMe was added in one portion. After 12 hours at rt, the reaction was-found complete by LCMS. The reactionwas diluted with EtOAc%hexane (4:1) (500ml). The organic phase was washed with 1N NaOH (2x80ml), water (2x80ml),sat. brine (80ml), dried with Na2SO4, filtered and concentrated under reduced pressure to give crude product. Theresidue was filtered through a filter plug of silica eluting with EtOAc/hexane (4:1). The fractions with product wereevaporated to give 8.02 g of product in 91 % yield.
91%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 12h;	Preparation of 2-{4-[4-(4-Amino-phenyl)-buta-1,3-diynyl)-benzoylamino\|-3-tert- butoxycarbonylamino-propionic acid methyl ester (2). DIEA (10.5 ml, 60.3 mmol) was added to a stirred solution of 4-[4-(4- Amino-phenyl)-buta-1,3-diynyl]-benzoic acid (1) (5.0 g, 19.1 mmol), HOBT (2.72 g, 20.1 mmol), EDC (3.85 g, 20.1 mmol) inDMF (80ml). After 2 min., H-DAP(Boc)-OMe (5.12 g, 2.1 mmol) was added in one portion. After 12 hours at rt, the reaction was found complete by LCMS. The reaction was diluted with EtOAc/hexane (4:1) (500 ml). The organic phase was washed with IN NaOH (2x80 ml), water (2x80 ml), sat. brine (80 ml), dried with Na2SO4, filtered and concentrated under reduced pressure to give crude product. The residue was filtered through a filter plug of silica eluting with EtOAc/hexane (4:1). The fractions with product were evaporated to give 8.02 g of (2) in 91 % yield.

Reference： [1]Patent: EP2295402,2015,B1 .Location in patent: Paragraph 0245; 0246
[2]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 100

40
[ 1093189-90-2 ]
[ 77087-60-6 ]
[ 1093189-99-1 ]

Yield	Reaction Conditions	Operation in experiment
68.1%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	Step 8. To a solution of compound (6) (44 mg, 0.126 mmol) and methyl 3-Boc-2, 3- diaminopropanoade (64 mg, 0.253 mmol) and PyBOP (131 mg, 0.253 mmol) in DMF (2mL) was added DIPEA (81 mg, 0.65 mmol). The reaction mixture was stirred at it. overnight and diluted with water (50 ml), extracted with EtOAc (50 ml x2). The combined organic layers were washed with water (50 ml x2), brine (50ml), dried (NaSO4) and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel eluting with MeOH/CH2Cl2 (0-5%) to give product 7 (47 mg, 68.1%, MS+ = 548.1).

Reference： [1]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 115-116

41
[ 506-59-2 ]
[ 501-53-1 ]
[ 77087-60-6 ]
[ 721927-33-9 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl (2S)-2-amino-3-[(tert-butoxycarbonyl)amino]propanoate (Synth. Comm., 23, 703(1993)) (1.24 g) was dissolved in methylene chloride (50 ml). Benzyl chloroformate (833 mul) and triethylamine (946 mul) were added, followed by stirring at room temperature for 15 hours. Water was added to the reaction mixture to separate the layers. The organic layer was washed with a 0.5N aqueous solution of hydrochloric acid and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in a mixed solvent of tetrahydrofuran (80 ml) and water (10 ml). Lithium hydroxide (143 mg) was added, followed by stirring at room temperature for 3 hours. The solvent was distilled off under reduced pressure. The residue was dissolved in N,N-dimethylformamide (50 ml). Dimethylamine hydrochloride (1.39 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.19 g) and 1-hydroxybenzotriazole (384 mg) were added. The resulting mixture was stirred overnight at room temperature. The solvent was distilled off under reduced pressure. Methylene chloride and water were added to the residue to separate the layers. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography (only ethyl acetate) on a silica gel column, whereby the title compound was obtained as a pale yellow oil (1.40 g).1H-NMR(CDCl3)delta: 1.42(9H,s), 2.92(3H,s), 3.13(3H,s), 3.20-3.30(1H,m), 3.37-3.47(1H,m), 4.78-4.85(1H,m), 5.05-5.14(2H,m), 5.22 (1H, br s), 6.11(1H, d, J=7.3Hz), 7.24-7.34(5H,m). MS (ESI)m/z: 366(M+H)+.

Reference： [1]Patent: EP1577302,2005,A1 .Location in patent: Page/Page column 200

42
[ 24424-99-5 ]
[ 18635-45-5 ]
[ 77087-60-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: D,L-α,β-diaminopropionic acid monohydrobromide With thionyl chloride In methanol at 0 - 20℃; for 17.5h; Heating / reflux; Stage #2: di-<i>tert</i>-butyl dicarbonate With triethylamine In dichloromethane at 0 - 20℃; for 17h;	14 hionyl chloride (7.26 ml) was added dropwise to methanol (100 ml) under ice cooling. The resulting mixture was stirred for 10 minutes under ice cooling. DL-2,3-Diaminopropionic acid hydrobromide (3.70 g) was added to the resulting solution in portions under ice cooling, followed by stirring at room temperature for 30 minutes, heating under reflux for 2 hours and stirring at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure. The residue was then suspended in methylene chloride (100 ml). Under ice cooling, triethylamine (11.1 ml) was added. After cooling to -78°C, a methylene chloride (50.0 ml) solution of di-tert-butyl dicarbonate (4.45 g) was added dropwise. The solution was returned gradually to room temperature and at room temperature, the solution was stirred for 16 hours. The reaction mixture was diluted with methylene chloride and washed successively with a saturated aqueous solution of sodium bicarbonate, water and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (100 g of silica gel, methylene chloride: methanol = 20:1), whereby the title compound (1.90 g) was obtained as a pale brown oil.1H-NMR(CDCl3) δ: 1.44(9H,s), 3.22-3.31(1H,m), 3.43-3.55(1H,m), 3.59(1H,t,J=5.7Hz), 3.75(3H,s), 5.10 (1H, br s). MS(ESI)m/z: 219(M+H)+.

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1577302, 2005, A1 Location in patent: Page/Page column 62

43
[ 619-86-3 ]
[ 77087-60-6 ]
[ 1003577-88-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2785 - 2795

44
[ 77087-60-6 ]
[ 142818-01-7 ]
[ 1003579-30-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2785 - 2795

45
[ 85217-69-2 ]
[ 77087-60-6 ]
[ 1265877-24-4 ]
(S)-methyl 3-((tert-butoxycarbonyl)amino)-2-(((R)-1-phenylallyl)amino)propanoate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 3153 - 3157

46
[ 77087-60-6 ]
(2E)-3-(2-thienyl)-2-propen-1-yl methyl carbonate [ No CAS ]
[ 1265877-26-6 ]
(S)-methyl 3-((tert-butoxycarbonyl)amino)-2-(((R)-1-(thiophen-2-yl)allyl)amino)propanoate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 3153 - 3157

47
[ 162558-25-0 ]
[ 77087-60-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 3153 - 3157

48
methyl N-α-(9-fluorenylmethyloxycarbonyl)-N-β-tert-butyloxycarbonyl-L-2,3-diaminopropionate [ No CAS ]
[ 77087-60-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 3153 - 3157

49
[ 77087-60-6 ]
[ 111-44-4 ]
[ 1260144-34-0 ]

Yield	Reaction Conditions	Operation in experiment
24%	With N-ethyl-N,N-diisopropylamine; at 127℃; for 18h;	7.1: Methyl(S)-3-tert-butoxycarbonylamino-2-morpholin-4-ylpropanoate 2.8 g (20 mmol) of 1-chloro-2-(2-chloroethoxy)ethane are added to a solution of 5 g (20 mmol) of commercial methyl(S)-2-amino-3-tert-butoxycarbonylaminopropanoate in 65 ml of diisopropylethylamine. The reaction mixture is stirred at 127 C. for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 1.4 g (24%) of methyl(S)-3-tert-butoxycarbonylamino-2-morpholin-4-ylpropanoate are obtained in the form of an oil.

Reference： [1]Patent: US2012/116072,2012,A1 .Location in patent: Page/Page column 15

50
[ 1694-92-4 ]
[ 77087-60-6 ]
[ 1384613-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; dichloromethane; at 0 - 20℃; for 1h;	Preparation of Compound DDA mixture of Compound CC (18.5 g, 83.8 mmol) and TEA (15.1 mL, 108.9 mmol) in DCM (200 mL) was cooled down to 0 C., followed by the dropwise addition of NosCl (20.5 g, 92.2 mmol) solution in THF (100 mL). The reaction was stirred for 1 h at 0 C. The reaction mixture was then allowed to rise to ambient temperature. Solvents were then removed in vacuo, and the residue was dissolved in EtOAc (800 mL), and washed with water (4×200 mL) and brine (200 mL). The organic layer was separated and dried over MgSO4. The solvent was removed in vacuo to afford crude Compound DD in 99% yield (33.3 g, 82.6 mmol) as a white solid. LC-MS [M+H] 403.7 (C15H21N3O8S+H, calc: 404.4). Compound DD was used directly in the next reaction without further purification.

Reference： [1]Patent: US2012/178773,2012,A1 .Location in patent: Page/Page column 26

51
[ 77087-60-6 ]
[ 1384613-21-1 ]

Reference： [1]Patent: US2012/178773,2012,A1

52
[ 77087-60-6 ]
[ 1384613-23-3 ]

Reference： [1]Patent: US2012/178773,2012,A1

53
[ 77087-60-6 ]
C₂₉H₄₁N₃O₉ [ No CAS ]

Reference： [1]Patent: US2012/178773,2012,A1

54
[ 77087-60-6 ]
C₂₈H₃₉N₃O₉ [ No CAS ]

Reference： [1]Patent: US2012/178773,2012,A1

55
[ 5703-26-4 ]
[ 77087-60-6 ]
methyl 3-[(tert-butoxy)carbonyl]amino}-2-[2-(4-methoxyphenyl)ethyl]amino}propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h;	99.d d) Methyl 3-[(tert-butoxy)carbonyl]amino}-2-[2-(4-methoxyphenyl) ethyl]amino)propanoate (I-56) d) Methyl 3-[(tert-butoxy)carbonyl]amino}-2-[2-(4-methoxyphenyl) ethyl]amino)propanoate (I-56) [0302] Sodium triacetoxyborohydride (2.21 g; 10.43 mmol; 1.1 eq) was added to a solution of 2-(4-methoxyphenyl)acetaldehyde (I-55) (1.28 g; 8.53 mmol; 0.9 eq) and methyl 2-amino-3-[(tert-butoxy)carbonyl]amino}propanoate (I-57) (2.07 g; 9.48 mmol; 1 eq) in dichloromethane (135 mL). The reaction mixture was stirred at room temperature for 16 hours. Saturated sodium hydrogenocarbonate (100 mL) was added. The aqueous layer was extracted with dichloromethane (2 x 130 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was first purified on silica gel using ethyl acetate/dichloromethane (1/9) as an eluent to afford the title compound, methyl 3-[(tert-butoxy)carbonyl]amino}-2-[2-(4-methoxyphenyl)ethyl]amino}propanoate in 80% yield (2.4 g) as an yellow oil. 1H NMR (CDCl3): δ 1.49 (s, 9H), 2.8 (m, 3H), 2.94 (m, 1H), 3.3 (m, 1H), 3.44 (m, 1H), 3.52 (m, 1H), 3.78 (s, 3H), 3.85 (s, 3H), 5.04 (m, 1H), 6.89 (d, 2H), 7.18 (d, 2H); MS (ESI+): m/z = 353.2 [(M+H]+
80%	With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h;	99.d d) Methyl 3-{ r(tert-butoxy)carbonyllamino)-2-{ Γ2-(4- methoxyphenyPethyll amino jpropanoate (1-56) d) Methyl 3-{ r(tert-butoxy)carbonyllamino)-2-{ Γ2-(4- methoxyphenyPethyll amino jpropanoate (1-56) Sodium triacetoxyborohydride (2.21 g; 10.43 mmol; 1.1 eq) was added to a solution of 2-(4-methoxyphenyl)acetaldehyde (1-55) (1.28 g; 8.53 mmol; 0.9 eq) and methyl 2-amino-3-{ [(iert-butoxy)carbonyl] amino Jpropanoate (1-57) (2.07 g; 9.48 mmol; 1 eq) in dichloromethane (135 mL). The reaction mixture was stirred at room temperature for 16 hours. Saturated sodium hydrogenocarbonate (100 mL) was added. The aqueous layer was extracted with dichloromethane (2 x 130 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was first purified on silica gel using ethyl acetate/dichloromethane (1/9) as an eluent to afford the title compound, methyl 3- { [(ieri-butoxy)carbonyl] amino } -2- { [2-(4-methoxyphenyl)ethyl] amino } propanoate in 80% yield (2.4 g) as an yellow oil. 1H NMR (CDC13): δ 1.49 (s, 9H), 2.8 (m, 3H), 2.94 (m, 1H), 3.3 (m, 1H), 3.44 (m, 1H), 3.52 (m, 1H), 3.78 (s, 3H), 3.85 (s, 3H), 5.04 (m, 1H), 6.89 (d, 2H), 7.18 (d, 2H); MS (ESI+): m/z = 353.2 [(M+H]+.

Reference： [1]Current Patent Assignee: VALNEVA SE - EP2664616, 2013, A1 Location in patent: Paragraph 0302-0303
[2]Current Patent Assignee: VALNEVA SE - WO2013/171281, 2013, A1 Location in patent: Page/Page column 150-151

56
4-((2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)carbamoyl)benzene-1-sulfonyl chloride [ No CAS ]
[ 77087-60-6 ]
(S)-methyl 2-(4-((2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyI)carbamoyI)phenylsulfonamido)-3-((tert-butoxycarbonyl)amino)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethylamine; In dichloromethane; at 0 - 20℃; for 7h;	The mixture of (S)-methyl 2-amino-3-((tert-butoxycarbonyl)amino)propanoate (0.93 g, 0.0042 mol,l eq) and triethylamine (1 mL) in dichloromethane (15 mL) was added dropwise to a solution of 4-((2- (2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)carbamoyl)benzene-l-sulfonyl chloride (1.8 g, 0.0042 mol, 1 eq) in CH2CI2(15 mL) at 0C. The reaction mixture was stirred at that temperature for 2h, and then for 5h by room temperature. Then, the reaction mixture was washed with water and brine. The organic layers were dried over MgS04and concentrated to get a residue, which was purified by column chromatography on silica gel (in-house system, cyclohexane / ethyl acetate = 1:1 ) to yield the title compound (2.3 g, 93%).HRMS: 625.2255 (M+Na+).*H NMR (400 MHz, CDCI3)6[ppm] 7.98 - 7.84 (m, 4H), 5.75 (s, 1H), 4.99 (s, 1H), 4.02 (s, 1H), 3.78 - 3.61 (m, 14H), 3.59(s, , 3H), 3.54 - 3.41 (m, 2H), 3.36 (t, 7=5.0, 2H), 1.95 (s, 1H), 1.54 - 1.34 (m, 9H).13C NMR (101 MHz, CDCI3)6[ppm] 170.06 , 165.84, 156.12, 142.11, 138.72, 127.99, 127.32, 80.24, 70.65, 70.52, 70.26,70.03, 69.54, 56.11, 53.04, 50.64, 43.27, 40.01, 28.25.

Reference： [1]Patent: WO2014/122228,2014,A1 .Location in patent: Page/Page column 25
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 9971 - 9982

57
[ 24424-99-5 ]
[ 6059-44-5 ]
[ 77087-60-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With triethylamine; In dichloromethane; at -78℃; for 2h;Inert atmosphere; Cooling with ice;	An amount of 10.0 g (0.053 mol) of compound 1 was suspended in 1 L of CH2CI2and kept in presence of argon at -78C. Triethylamine (30 ml, 0.20 mol) was added dropwise to the cold suspension to obtain a solution mixture. Di-r-butyldicarbonate (11.6 g, 0.054 mol) was dissolved in 100 mL CH2CI2and added dropwise to the mixture. After the addition was completed the reaction was placed in an ice bath and stirred for 2h. The reaction was transferred to a separation funnel and extracted with 2 x 50 mL of 10% Na2S04solution. After the aqueous layer was washed with 3 x 10 mL CH2CI2, the pH was adjusted to 10 using saturated NaHC03and 3N NaOH solutions, it was extracted with 10 x 100 mL of CH2CI2. The organic layer was dried over MgS04;filtered and concentrated to obtain 4.9 g of a pale yellow oil. Column chromatography on silica gel in 2.5%MeOH/ EtOAc resulted 4.32g of the product (53%).HRMS: 219.1324 (M+H+), 241.11436 (M+Na+).*H NMR (300 MHz, CDCI3): 6[ppm]= 5.11 (s, 1H), 3.78 - 3.69 (s, 3H), 3.60 - 3.46 (m, 2H), 3.31- 3.15 (m, 1H), 1.64 (s, 2H),1.42 (s, 9H).13C MR (75 MHz, CDCI3):5[ppm]= 174.46, 155.94, 79.48, 54.36, 52.26, 44.16, 28.30.

Reference： [1]Patent: WO2014/122228,2014,A1 .Location in patent: Page/Page column 23; 24
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 9971 - 9982

58
[ 77087-60-6 ]
methyl (S)-2-(4-hydroxyphenylsulfonamido)-3-[(tertbutoxycarbonyl)amino]propanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 9971 - 9982

59
[ 77087-60-6 ]
methyl 2-[4-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethoxy)phenylsulfonamido]-3-[(tert-butoxycarbonyl)amino]propanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 9971 - 9982

60
3-[(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethyl)carbamoyl]benzene-1-sulfonyl chloride [ No CAS ]
[ 77087-60-6 ]
C₂₄H₃₈N₆O₁₀S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 9971 - 9982

61
[ 77087-60-6 ]
[ 87001-32-9 ]
methyl (S)-2-[4-(benzyloxy)phenylsulfonamido]-3-[(tertbutoxycarbonyl)amino]propanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 9971 - 9982

62
[ 77087-60-6 ]
[ 98-74-8 ]
C₁₅H₂₁N₃O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 0.5h;	Compound I (3.5 g, 22.4 mmol, 1.0 eq) and diisopropylethylamine (11.7 mL, 67.2 mmol, 3.0 eq) were dissolved in DCM (70 mL) and cooled to 0 C. A solution of nosylchloride (4.95 g, 22.4 mmol, 1.0 eq), dissolved in DCM (30 mL), was then added dropwise to the solution. The reaction was stirred for 30 minutes, then transferred to a separatory funnel and diluted with DCM (~100 mL). The DCM solution was then washed with 1 M HCl(aq), saturated NaHCO3 solution, water, then brine. The organic layer was then dried over MgSO4, filtered, then concentrated to produce light yellow crystals. The light yellow crystals were dissolved in DMF (~75 mL). Cs2CO3 (21.84 g, 67.2 mmol, 3.0 eq) was added followed by iodomethane (1.39 mL, 22.4 mmol, 1.0 eq). The reaction was stirred at room temperature for 3 hours, water was added to dissolve remaining Cs2CO3 salts, then the mixture was transferred to a separatory funnel and diluted with EtOAc (~200 mL). The EtOAc solution was washed with 1 M HCl (100 mL), saturated NaHCO3 solution(100 mL), water(100 mL), then brine (100 mL). The organic layer was dried over MgSO4, filtered, then concentrated to produce a light yellow crystalline solid. The resulting solid was dissolved in DCM (150 mL) and treated with 4N HCl in dioxane (10 mL) and stirred at RT for 3 hours. The reaction was concentrated and placed under high vacuum to remove any residual solvents resulting in the isolation of a viscous light yellow residue. The resulting residue was dissolved in DMF (50 mL) followed by the addition of HATU (9.36 g, 22.4 mmol, 1.1 eq) and Boc-Arg(Pmc)-OH (12.7 g, 22.4 mmol, 1.0 eq). The solution was cooled to -78 C and DIPEA (11.7 mL, 67.2 mmol, 3.0 eq) was added dropwise with vigorous stirring. The reaction was allowed to warm to RT and stirred for an additional 2 hours. The concentrated reaction was diluted with EtOAc (100 mL) and transferred to a separatory funnel. The EtOAc solution was washed with 1 M HCl (100 mL), saturated NaHCO3 solution(100 mL), water(100 mL), then brine(100 mL). The organic layer was dried over MgSO4, filtered, then concentrated to produce a light yellow crystalline solid. The resulting solid was dissolved in DCM (150 mL) and treated with 4N HCl in dioxane (15 mL) and stirred at RT for 3 hours. The reaction was concentrated and placed under high vacuum to remove any residual solvents resulting in the isolation of a viscous light yellow residue. The resulting residue was dissolved in DCM (150 mL) and diisopropylethylamine (11.7 mL, 67.2 mmol, 3.0 eq) was added followed by the addition of solid AcN-Gly-ONp (0.53 g, 22.4 mmol, 1.0 eq) in one portion. The reaction was stirred at RT for 2 hours, concentrated on a rotary evaporator, then purified using preparative HPLC (C-18 column employing a method of 20-100% acetonitrile (ACN) with a 20 minute ramp) to afford 8.30 g (10 mmol, 47 % overall yield) of the methyl ester form of Intermediate J as a white solid following lyophilization of the collected fractions. The methyl ester form of Intermediate J was dissolved in 5:1 methanol (MeOH): water. Next, LiOH (0.24 g, 100 mmol, 10 eq) was added and the reaction was stirred at RT for several hours. The reaction was neutralized to pH ~4-5 with acetic acid (AcOH) and concentrated on a rotary evaporator. The resulting Intermediate J was used without further purification. LC-MS [M+H]: 825.1 (C34H48N8O12S2+H, calc: 824.3).

Reference： [1]Patent: WO2015/4029,2015,A1 .Location in patent: Page/Page column 17
[2]Patent: WO2018/170465,2018,A1 .Location in patent: Paragraph 271

63
[ 619-58-9 ]
[ 77087-60-6 ]
3-tert-butoxycarbonylamino-(2S)-2-(4-iodobenzoylamino)propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		DIEA (9.7ml, 55.1mmol) was added to a stirred solution of 4-iodo-benzoic acid (5.49g, 22.2mmol), HOAT (3.08g,22.6mmol), EDC (4.33g, 22.6mmol) in DMF (85ml). After 2 min., the H-DAP(Boc)-OMe (1) was added in one portion.After 12 hours, the reaction was found complete by LCMS. The reaction was diluted with EtOAc/hexane (1:1) (500ml).The organic phase was washed with 1N HCl (2x80ml), 1N NaOH (2x80ml), water (2x80ml), sat. brine (80ml), dried withNa2SO4, filtered and concentrated under reduced pressure to give crude product. The residue was filtered through afilter plug of silica eluting with EtOAc/hexane (1:1). The fractions with product were evaporated to give 9.3 g of product(3-tert-Butoxycarbonylamino-2-(4-iodo-benzoylamino)-propionic acid methyl ester) in 93% yield. This product was convertedto analogues in a similar manner as the aforementioned Examples.

Reference： [1]Patent: EP2295402,2015,B1 .Location in patent: Paragraph 0214; 0215

64
[ 77087-60-6 ]
methyl2-[2-amino-3-(tert-butoxycarbonylamino)propanamido]-3-(tert-butoxycarbonylamino)propanoate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7015 - 7022

65
[ 77087-60-6 ]
tert-butyl (3,6-dioxopiperazine-2,5-diyl)bis(methylene)dicarbamate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7015 - 7022

66
[ 16947-84-5 ]
[ 77087-60-6 ]
methyl 5-[(tert-butoxycarbonylamino)methyl]-13,13-dimethyl-3,6,11-trioxo-1-phenyl-2,12-dioxa-4,7,10-triazatetradecane-8-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7015 - 7022

67
[ 88425-46-1 ]
[ 77087-60-6 ]
methyl (S)-3-amino-2-((S)-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of N- benzenesulfonyl proline (10 mmol) in DMF (50 mL) were added DIPEA (2 eq) and HCTU (leq). After stirring 1 minute to obtain a clear solution, the amine shown in the above reaction scheme (10 mmol) in DMF (5 mL) was added to the mixture and stirred overnight at room temperature. The mixture was diluted with ethyl acetate and washed with saturated NaHC03 solution and dried over Na2S04. After concentration under reduced pressure, the crude product was dissolved in 50% TFA (25 mL) in DCM and stirred for 2.5h. The volatiles were blown off by a stream of N2 and the residue was neutralized by addition of sat. Na2C03 solution. The product was extracted with DCM and dried over Na2S04 to yield the following amine product: methyl (S)-3-amino-2-((S)-l-(phenylsulfonyl)pyrrolidine-2-carboxamido)propanoate : ESI-MS 356.7 (MH+).

Reference： [1]Patent: WO2017/173302,2017,A2 .Location in patent: Paragraph 0589

68
[ 77087-60-6 ]
C₁₆H₂₃N₃O₈S [ No CAS ]

Reference： [1]Patent: WO2018/170465,2018,A1

69
[ 77087-60-6 ]
[ 609820-09-9 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 2466 - 2484

70
[ 112-80-1 ]
[ 77087-60-6 ]
methyl (2S)-3-(tert-butoxycarbonylamino)-2-[[(Z)-octadec-9-enoyl]amino]propanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 2466 - 2484

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P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
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.
P283	Wear fire/flame resistant/retardant clothing.
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:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 77087-60-6 ] {[proInfo.proName]}

Quality Control of [ 77087-60-6 ]

Related Doc. of [ 77087-60-6 ]

Product Details of [ 77087-60-6 ]

Safety of [ 77087-60-6 ]

Application In Synthesis of [ 77087-60-6 ]

[ 77087-60-6 ] Synthesis Path-Upstream 1~10

[ 77087-60-6 ] Synthesis Path-Downstream 1~70

Related Functional Groups of [ 77087-60-6 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 77087-60-6 ]