[ CAS No. 100927-10-4 ] {[proInfo.proName]}

Name: 100927-10-4|(R)-tert-Butyl (1-aminopropan-2-yl)carbamate|98%
Brand: Ambeed
SKU: A164387
Price: 10.0 USD
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Quality Control of [ 100927-10-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 100927-10-4 ]

CAS No. :	100927-10-4	MDL No. :	MFCD11112229
Formula :	C₈H₁₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JQXZBJAAOLPTKP-ZCFIWIBFSA-N
M.W :	174.24	Pubchem ID :	45072490
Synonyms :

Calculated chemistry of [ 100927-10-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.88
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	47.79
TPSA :	64.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	0.42
Log Po/w (WLOGP) :	0.86
Log Po/w (MLOGP) :	0.63
Log Po/w (SILICOS-IT) :	-0.03
Consensus Log Po/w :	0.8

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.85
Solubility :	24.3 mg/ml ; 0.14 mol/l
Class :	Very soluble
Log S (Ali) :	-1.34
Solubility :	7.99 mg/ml ; 0.0459 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.31
Solubility :	8.55 mg/ml ; 0.0491 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.46

Safety of [ 100927-10-4 ]

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:

Application In Synthesis of [ 100927-10-4 ]

* 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 [ 100927-10-4 ]
Downstream synthetic route of [ 100927-10-4 ]

[ 100927-10-4 ] Synthesis Path-Upstream 1~9

1
[ 146610-69-7 ]
[ 100927-10-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 15 h;	To a stirred solution of (S)-tert-butyl 1-azidopropan-2-ylcarbamate (S2-3) (6.0 g, 30 mmol) in ethyl acetate (50.0 mL), 10percent Pd/C (2.3 g) was added. The reaction mixture was stirred under a hydrogen atmosphere (1 atm) for 15 h at room temperature. The reaction mixture was filtered through celite, the celite was washed with ethyl acetate and the filtrate was concentrated under reduced pressure to obtain the title compound S2-4 (4.8 g, 92percent) as a pale yellow solid. ¹H NMR (400 MHz, DMSO-d₆) δ 0.95 (d, J=6.6 Hz, 3H), 1.36 (s, 9H), 2.49 (m, 2H), 3.32 (m, 1H), 6.49 (br s, 1H)

Reference： [1] Patent: US2016/75720, 2016, A1, . Location in patent: Paragraph 0247

2
[ 78981-25-6 ]
[ 100927-10-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With borane-THF In tetrahydrofuran at 20 - 70℃; for 18 h; Inert atmosphere	To a stirred solution of Boc-D-Ala-NH₂ (4.600 g, 24.4 mmol, 1.0 equiv.) in anhydrous tetrahydrofuran (100 mL) under nitrogen was added 1.0 M borane-tetrahydrofuran complex in tetrahydrofuran (97.756 mL, 97.8 mmol, 4.0 equiv.). The mixture was stirred for 16 h at room temperature and then heated at 70° C. for 2 h. After cooling, the reaction was quenched with methanol until no bubbles generated. The mixture was heated at 70° C. for 2 h and then concentrated in vacuo. The residue was purified by silica gel column (0-30percent methanol/methylene chloride) to afford the desired product as a colorless oil (1.5 g, 35percent). ¹H NMR (300 MHz, CDCl₃): δ 4.60 (br s, 1H), 3.65 (m, 1H), 2.75 (dd, 1H, J=12.9, 5.1 Hz), 2.63 (dd, 1H, J=12.9, 6.6 Hz), 1.45 (s, 9H), 1.41 (s, 2H), 1.12 (d, 3H, J=6.3 Hz).

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6814 - 6824
[2] Patent: US2015/284362, 2015, A1, . Location in patent: Paragraph 0416
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4878 - 4881
[4] Patent: WO2016/206101, 2016, A1, . Location in patent: Page/Page column 358; 359

3
[ 79069-13-9 ]
[ 100927-10-4 ]

Reference： [1] Bioscience, Biotechnology and Biochemistry, 2011, vol. 75, # 4, p. 780 - 782
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2877 - 2879
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6305 - 6312,8
[4] Patent: US2016/75720, 2016, A1,
[5] Patent: WO2006/116764, 2006, A1,

4
[ 1352719-38-0 ]
[ 100927-10-4 ]

5
[ 126301-16-4 ]
[ 100927-10-4 ]

Reference： [1] Patent: US2016/75720, 2016, A1,
[2] Patent: WO2006/116764, 2006, A1,

6
[ 721927-55-5 ]
[ 100927-10-4 ]

Reference： [1] Patent: WO2006/116764, 2006, A1, . Location in patent: Page/Page column 123

7
[ 3744-87-4 ]
[ 100927-10-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6814 - 6824

8
[ 24424-99-5 ]
[ 100927-10-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2877 - 2879
[2] Patent: US2016/75720, 2016, A1,

9
[ 91103-47-8 ]
[ 100927-10-4 ]

Reference： [1] Patent: US2015/284362, 2015, A1,

[ 100927-10-4 ] Synthesis Path-Downstream 1~35

1
[ 824398-03-0 ]
[ 100927-10-4 ]
[ 824399-45-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2007,vol. 55,p. 881 - 889

2
[ 100927-10-4 ]
[ 78-84-2 ]
[ 1309563-13-0 ]

Reference： [1]Patent: WO2006/116764,2006,A1 .Location in patent: Page/Page column 123

3
[ 721927-55-5 ]
[ 100927-10-4 ]

Reference： [1]Patent: WO2006/116764,2006,A1 .Location in patent: Page/Page column 123

4
[ 100927-10-4 ]
[ 1188365-72-1 ]
methyl 1-[[(2R)-2-(tert-butoxycarbonylamino)propyl]amino]thieno[3,2-f]quinoline-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 110℃; for 16.0h;	To a solution of methyl 1-bromothieno[3,2-f]quinoline-2-carboxylate (S1-5) (14 g, 43.4 mmol) in toluene (140 mL), cesium carbonate (28.3 g, 86.9 mmol) and <strong>[100927-10-4](R)-tert-butyl 1-aminopropan-2-ylcarbamate</strong> (11.3 g, 65.0 mmol, prepared as described in Scheme 2, below) were added at room temperature and degassed for 15 min. To the resulting mixture, BINAP (2.7 g, 4.3 mmol) and Pd2(dba)3 (3.9 g, 4.3 mmol) were added at room temperature and again degassed for 10 min. The resulting reaction mixture was stirred at 110 C. for 16 h. After completion, the reaction mixture was filtered through celite and washed with ethyl acetate and concentrated under reduced pressure. The crude material obtained was purified by column chromatography to afford the title compound S1-6 (12 g, 66%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): delta 1.01 (d, J=6.5 Hz, 3H), 1.34 (s, 9H), 3.12 (m, 2H), 3.63 (m, 1H), 3.88 (s, 3H), 6.55 (t, J=7.0 Hz, 1H), 6.71 (br s, 1H), 7.70 (dd, J=4.2 Hz, 8.3 Hz, 1H), 8.04 (d, J=9.0 Hz, 1H), 8.21 (d, J=9.0 Hz, 1H), 8.94 (d, J=3.9 Hz, 1H), 9.04 (d, J=8.3 Hz, 1H). MS m/z (M+H): 416.1

Reference： [1]Patent: US2016/75720,2016,A1 .Location in patent: Paragraph 0229; 0234
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4882 - 4884

5
[ 100927-10-4 ]
[ 1188365-75-4 ]
C₂₆H₂₈N₂O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4882 - 4884

6
[ 100927-10-4 ]
[ 1188365-66-3 ]
C₂₀H₂₄N₂O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4882 - 4884

7
[ 100927-10-4 ]
[ 1188365-67-4 ]
C₂₀H₂₆N₂O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4882 - 4884

8
[ 100927-10-4 ]
[ 41280-81-3 ]
[ 400652-22-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4878 - 4881

9
[ 78981-25-6 ]
[ 100927-10-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With borane-THF; In tetrahydrofuran; at 20 - 70℃; for 18.0h;Inert atmosphere;	To a stirred solution of Boc-D-Ala-NH2 (4.600 g, 24.4 mmol, 1.0 equiv.) in anhydrous tetrahydrofuran (100 mL) under nitrogen was added 1.0 M borane-tetrahydrofuran complex in tetrahydrofuran (97.756 mL, 97.8 mmol, 4.0 equiv.). The mixture was stirred for 16 h at room temperature and then heated at 70 C. for 2 h. After cooling, the reaction was quenched with methanol until no bubbles generated. The mixture was heated at 70 C. for 2 h and then concentrated in vacuo. The residue was purified by silica gel column (0-30% methanol/methylene chloride) to afford the desired product as a colorless oil (1.5 g, 35%). 1H NMR (300 MHz, CDCl3): delta 4.60 (br s, 1H), 3.65 (m, 1H), 2.75 (dd, 1H, J=12.9, 5.1 Hz), 2.63 (dd, 1H, J=12.9, 6.6 Hz), 1.45 (s, 9H), 1.41 (s, 2H), 1.12 (d, 3H, J=6.3 Hz).
	In tetrahydrofuran; at 20 - 70℃; for 4.0h;	Intoa 500 mL round bottom flask, borane (20m1, 200 mmol) was added dropwise to a stirred mixture of (R)-tert-butyl (1-amino-i -oxopropan-2-yl)carbamate (15 .OOg, 80 mmol) in THF (150 ml)at room temperature. After the resulting mixture was stirred at 70C for 4 hr, it was cooled down to room temperature, quenched with sodium hydroxide (iN) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (3 x 40mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with ethyl acetate/petroleum/ether (1/1) to give the title compound as an oil. LCMS (ESI) calc?d for C8H,8N202 [M + H]:175,found:175. ?H NMR (300 MHz, DMSO-d6):3.88-3.79 (m, 2H), 2.66- 2.62 (m, 1H), 1.49 (s, 9H), 1.16 (d,J=5.7Hz, 3H).

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6814 - 6824
[2]Patent: US2015/284362,2015,A1 .Location in patent: Paragraph 0416
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4878 - 4881
[4]Patent: WO2016/206101,2016,A1 .Location in patent: Page/Page column 358; 359

10
[ 100927-10-4 ]
[ 82674-16-6 ]
[ 1363484-01-8 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2011,vol. 75,p. 780 - 782

11
[ 1352719-38-0 ]
[ 100927-10-4 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2011,vol. 75,p. 780 - 782
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2877 - 2879
[3]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6305 - 6312,8

12
[ 79069-13-9 ]
[ 100927-10-4 ]

13
[ 100927-10-4 ]
[ 4878-36-8 ]
[ 1373437-46-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2877 - 2879

14
[ 24424-99-5 ]
[ 100927-10-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2877 - 2879
[2]Patent: US2016/75720,2016,A1

15
[ 100927-10-4 ]
[ 70258-18-3 ]
[ 1363484-01-8 ]

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6305 - 6312,8

16
[ 100927-10-4 ]
[ 1383724-17-1 ]

Reference： [1]Patent: US2013/274269,2013,A1

17
[ 100927-10-4 ]
[ 1383724-18-2 ]

Reference： [1]Patent: US2013/274269,2013,A1

18
[ 100927-10-4 ]
[ 17199-29-0 ]
[ 1383724-69-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;	Example 107 (S)-2-hydroxy-N-{(R)-2-(isoquinoline-6-sulfonamido)propyl}-2-phenylacetamide hydrochloride The title compound was synthesized according to the following Scheme 29: (S)-mandelic acid (261 mg) and <strong>[100927-10-4](R)-tert-butyl 1-aminopropan-2-ylcarbamate</strong> (300 mg) were condensed (423 mg, 80%) using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (363 mg) and 1-hydroxybenzotriazole (232 mg) in dichloromethane. Subsequently, the Boc group was removed with a 4 M hydrochloric acid-1,4-dioxane solution (2 mL), and the resulting amine compound and isoquinoline-6-sulfonyl chloride prepared in Reference Example 1 were condensed (370 mg, 67%).

Reference： [1]Patent: US2013/274269,2013,A1 .Location in patent: Paragraph 0642

19
[ 100927-10-4 ]
[ 22098-20-0 ]
[ 1383724-16-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 12.0h;	2.66 g of (S)-2-hydroxy-2-(thiophen-3-yl)acetic acid obtained by the optical resolution of 2-hydroxy-2-(thiophen-3-yl)acetic acid with lipase, 454 mg of 1-hydroxybenzotriazole, and 3.87 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added thereto, and the mixture was stirred at room temperature for 12 hours. 100 mL of dichloromethane was added thereto, and the organic layer was washed with water (30 mL*5) and saturated saline and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2) to obtain 4.0 g of the compound of interest (75%).

Reference： [1]Patent: US2013/274269,2013,A1 .Location in patent: Paragraph 0279

20
[ 100927-10-4 ]
dimethyl 3-bromobenzo[b]thiophene-2,5-dicarboxylate [ No CAS ]
(R)-dimethyl 3-(2-(tert-butoxycarbonylamino)propylamino)benzo[b]thiophene-2,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; for 48.0h;	(R)-Dimethyl-3-(2-(tert-butoxycarbonylamino) propylamino) benzo[b]thiophene-2, 5-dicarboxylate (5). To a solution of dimethyl-3- bromobenzo[b]thiophene-2, 5-dicarboxylate (2.0 g, 6.0 mmol) and (R)-tert-butyl 1-aminopropan- 2-ylcarbamate (1.3 g, 7.0 mmol) in toluene (30 mL), cesium carbonate (3.9 g, 12 mmol) was added, and the resulting solution was degassed for 10 min. To this mixture, BINAP (381.0 mg, 0.6 mmol) and trisdibenzylidenedipalladium (56mg, 0.6 mmol) were added and further degassed for another 5 min. The resulting mixture was refluxed at 80 C for 48h. After completion of the reaction, the reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to yield 5 (1.5 g, 59%) as a pale yellow solid. 1H NMR (400 MHz, CDC13) delta 1.29 (d, J = 6.7 Hz, 3H), 1.40 (s, 9H), 3.75 (m, 1H), 3.88 (s, 3H), 3.90 (s, 3H), 3.96 (m, 1H), 4.6 (brs, 1H), 7.51 (m, 1H), 7.75 (d, J = 8.5 Hz, 1H), 8.04-8.07 (dd, J = 1.5, 8.5 Hz, 1H), 8.74 (d, J = 0.8 Hz, 1H).

Reference： [1]Patent: WO2014/149164,2014,A1 .Location in patent: Paragraph 00712

21
[ 100927-10-4 ]
[ 1402144-13-1 ]
(R)-ethyl 1-(2-(tert-butoxycarbonylamino)propylamino)thieno[3,2-f]quinoline-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 110℃; for 16.0h;	(R)-ethyl l-(2-(tert-butoxycarbonylamino)propylamino)thieno [3,2-f] quinoline-2- carboxylate (5). To a solution of ethyl- 1-bromothieno [3, 2-f] quinoline-2-carboxylate (2.0 g, 6.0 mmol) and (R)-tert-butyl l-aminopropan-2-ylcarbamate (1.2 g, 7.2 mmol) in toluene (60.0 mL), cesium carbonate (3.9 g, 12.0 mmol) was added and degassed for 10 min. BINAP (374.0 mg, 0.6 mmol) and Pd2(dba)3 (550 mg, 0.6 mmol) were added and again degassed for another 5 min. The resulting mixture was heated at 110 C for 16 h. The reaction mixture was filtered through celite and the filtrate was partitioned between water (100 mL) and ethyl acetate (150 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduce pressure. The residue was purified by silica gel column chromatography to afford 5 (1.0 g, 39%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 1.0 (t, J = 6.5 Hz, 3H ), 1.33 (t, J = 4.8 Hz, 3H), 1.38 (s, 9H), 3.1 (t, J = 6.4 Hz, 2H), 3.63 (brs, 1H), 4.34 (q, J = 7.0 Hz, 2H), 6.53 (t, J = 6.3 Hz, 1H), 6.76 (d, J = 8.1 Hz, 1H), 7.70 (q, J = 4.2 Hz, 1H), 8.05 (d, J = 9.0 Hz, 1H), 8.21 (d, J = 8.9 Hz, 1H), 8.92-8.94 (dd, J = 1.5, 4.2 Hz, 1H), 9.03 (d, J = 8.3 Hz, 1H).

Reference： [1]Patent: WO2014/149164,2014,A1 .Location in patent: Paragraph 00735

22
[ 100927-10-4 ]
ethyl 3-bromo-5-(2-chloropyridin-4-yl)thiophene-2-carboxylate [ No CAS ]
(R)-ethyl 3-(2-(tert-butoxycarbonylamino)propylamino)-5-(2-chloropyridin-4-yl)thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 120℃; for 12.0h;	(R)-Ethyl 3-(2-(tert-butoxycarbonylamino) propylamino)-5-(2-chloropyridin-4- yl) thiophene-2-carboxylate (6). To a stirred solution of Ethyl 3-bromo-5-(2-chloropyridin-4-yl) thiophene-2-carboxylate (400 mg, 1 mmol) in toluene (20.0 mL), (R)-tert-butyl 1-aminopropan- 2-ylcarbamate (403 mg, 2 mmol), Pd2(dba)3 (106 mg, 0.1 mmol), cesium carbonate (755 mg, 2 mmol) and BINAP (72 mg, 0.1 mmol) were added and degassed for 15 min. The resulting mixture was heated at 120 C for 12 h. The reaction mixture was concentrated and separated between ethyl acetate (100 mL) and water (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography to obtain 6 (200 mg, 39%) as a yellow solid. 1H NMR (400 MHz, DMSO-dg) delta 1.06 (d, J = 6.6 Hz, 3H), 1.25 (t, J = 7.0 Hz, 3H), 1.31 (s, 9H), 3.22 (m, 1H), 3.38 (m, 1H), 3.65 (m, 1H), 4.22 (q, J = 7.0 Hz, 2H), 6.85 (d, J = 8.1 Hz, 1H), 6.97 (d, J = 6.2 Hz, 1H), 7.66-7.68 (dd, J =1.5, 5.2 Hz, 1H), 7.75 (s, 1H), 7.92 (d, J = 1.2 Hz, 1H), 8.43 (d, J = 5.2 Hz, 1H). MS m/z (M+H): 440.2

Reference： [1]Patent: WO2014/149164,2014,A1 .Location in patent: Paragraph 00773

23
[ 100927-10-4 ]
[ 98948-96-0 ]
(R)-methyl 3-((2-((tert-butoxycaronyl)amino)propyl)amino)-5-nitrobenzo[b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6814 - 6824

24
[ 3744-87-4 ]
[ 100927-10-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6814 - 6824

25
[ 100927-10-4 ]
(R)-3,6-difluoro-9-(oxiran-2-ylmethyl)-9H-carbazole [ No CAS ]
tert-butyl ((R)-1-(((S)-3-(3,6-difluoro-9H-carbazol-9-yl)-2-hydroxypropyl)amino)propan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol; at 70℃; for 15.0h;	A mixture of (R)-3,6-difluoro-9-(oxiran-2-ylmethyl)-9H-carbazole (0.200 g, 0.8 mmol, 1.0 equiv.) and <strong>[100927-10-4](R)-tert-butyl (1-aminopropan-2-yl)carbamate</strong> (0.403 g, 2.3 mmol, 3.0 equiv.) in ethanol (10 mL) was stirred at 70 C. After 15 h, the reaction mixture was concentrated in vacuo and purified by silica gel column (0-30% methanol/methylene chloride) to isolate the desired product as a white powder (0.250 g, 75%). 1H NMR (300 MHz, CDCl3): delta 7.68 (dd, 2H, J=8.7, 2.7 Hz), 7.41 (dd, 2H, J=9.3, 4.2 Hz), 7.22 (td, 2H, J=9.3, 2.4 Hz), 4.43 (br s, 1H), 4.35 (d, 2H, J=5.7 Hz), 4.12 (m, 1H), 3.78 (br s, 1H), 2.80 (dd, 1H, J=12.3, 3.6 Hz), 2.63 (dd, 1H, J=12.3, 5.7 Hz), 2.57 (d, 2H, J=7.2 Hz), 1.44 (s, 9H), 1.11 (d, 3H, J=6.6 Hz); ESI (m/z): 434.0 (M+H).

Reference： [1]Patent: US2015/284362,2015,A1 .Location in patent: Paragraph 0418

26
[ 100927-10-4 ]
(R)-9-(oxiran-2-ylmethyl)-9H-carbazole [ No CAS ]
tert-butyl ((R)-1-(((S)-3-(9H-carbazol-9-yl)-2-hydroxypropyl)amino)propan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; at 70℃; for 15.0h;	A mixture of (R)-9-(oxiran-2-ylmethyl)-9H-carbazole (0.150 g, 0.7 mmol, 1.0 equiv.) and <strong>[100927-10-4](R)-tert-butyl (1-aminopropan-2-yl)carbamate</strong> (0.351 g, 2.0 mmol, 3.0 equiv.) in ethanol (10 mL) was stirred at 70 C. After 15 h, the reaction mixture was concentrated in vacuo and purified by silica gel column (0-30% methanol/methylene chloride) to isolate the desired product as a white foam (0.210 g, 78%). 1H NMR (300 MHz, CDCl3): delta 8.10 (d, 2H, J=7.5 Hz), 7.55-7.40 (m, 4H), 7.27-7.20 (m, 2H), 4.60-4.30 (m, 3H), 4.16 (m, 1H), 3.78 (m, 1H), 2.80 (dd, 1H, J=12.3, 3.6 Hz), 2.67 (dd, 1H, J=12.0, 8.4 Hz), 2.60-2.50 (m, 2H), 1.44 (s, 9H), 1.10 (d, 3H, J=6.6 Hz); ESI (m/z): 398.1 (M+H).

Reference： [1]Patent: US2015/284362,2015,A1 .Location in patent: Paragraph 0420

27
[ 91103-47-8 ]
[ 100927-10-4 ]

Reference： [1]Patent: US2015/284362,2015,A1

28
[ 126301-16-4 ]
[ 100927-10-4 ]

Reference： [1]Patent: US2016/75720,2016,A1
[2]Patent: WO2006/116764,2006,A1

29
[ 146610-69-7 ]
[ 100927-10-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20℃; under 760.051 Torr; for 15.0h;	To a stirred solution of (S)-tert-butyl 1-azidopropan-2-ylcarbamate (S2-3) (6.0 g, 30 mmol) in ethyl acetate (50.0 mL), 10% Pd/C (2.3 g) was added. The reaction mixture was stirred under a hydrogen atmosphere (1 atm) for 15 h at room temperature. The reaction mixture was filtered through celite, the celite was washed with ethyl acetate and the filtrate was concentrated under reduced pressure to obtain the title compound S2-4 (4.8 g, 92%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 0.95 (d, J=6.6 Hz, 3H), 1.36 (s, 9H), 2.49 (m, 2H), 3.32 (m, 1H), 6.49 (br s, 1H)

Reference： [1]Patent: US2016/75720,2016,A1 .Location in patent: Paragraph 0247

30
[ 100927-10-4 ]
[ 501-53-1 ]
(R)-benzyl tert-butyl propane-1,2-diyldicarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 2.0h;	Into a 100 mL round bottom flask, benzyl carbonochloridate (5.87 g, 34.4 mmol) was added dropwise to a stirred mixture of triethylamine (5.23 g, 51.7 mmol),(R)-tert-butyl 1- aminopropan-2-ylcarbamate(4.00 g,22.00 mmol) in DCM (20 ml) at room temperature. The reaction mixture was stirred at room temperature for 2 hr and then was diluted with water (50 mL) and extracted with ethyl acetate (3x 50 mL). The combined organic layers were washed with brine (2 x 25 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with ethyl acetate/petroleum ether (1/10) to givethe title compound as a solid. LCMS (ESI) calc?d for C,6H24N204 [M + H]:309, found:309. ?H NMR (300 MHz, DMSO-d6): 7.4 1- 715 (m, 5H), 5.04 (s, 2H), 4.63-4.55 (m, 1H),3.69-3.51(m,1H),3.25-3.18(m,1H),1.35(s, 8H), 1.06(d, J =6.9 Hz 3 H).

Reference： [1]Patent: WO2016/206101,2016,A1 .Location in patent: Page/Page column 363

31
[ 100927-10-4 ]
2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-iodo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)benzenesulfinic acid [ No CAS ]
(R)-tert-butyl (1-(2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-iodo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenylsulfonamido)propan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Into a 50 mL round bottom flask, 1-chloropyrrolidine-2,5-dione (172 mg, 1.289 mmol) was added to a stirred mixture of 2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-iodo-3-(2- (4-methoxybenzyl)-2H-tetrazol-5 -yl)benzenesulfinic acid (500mg, 0.645 mmol) in tetrahydrofuran (20 ml) at room temperature. The reaction mixture was stirred at room temperature for 1 hr. The reaction was determined to be complete by LCMS. (R)-tert-butyl 1- aminopropan-2-ylcarbamate (0.1 7g, 1.289 mmol) was added to the reaction mixture under room temperature. The reaction mixture was stirred at room temperature for overnight. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (3x lOOmL). The combined organic layers were washed with brine (1 x 60 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluting with ethyl acetate/petroleum ether(1/5) to give the title compound as a solid. LCMS (ESI) calc?d for C39H461N70952 [M + H]:948,found:948. ?H NMR (300 MHz, CDC13):8.42-8.24 (m, 4H), 7.33-7.26 (m, 4H), 6.96-6.86(m,6H), 5.80 (s, 2H), 4.10-3. 70(m, 4H),3.79(s,9H),3.70-3.68(m,3H),1 .47(s,9H),1 . 16(d,J = 3.0Hz, 3H).

Reference： [1]Patent: WO2016/206101,2016,A1 .Location in patent: Page/Page column 359

32
[ 100927-10-4 ]
2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-iodo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)benzenesulfinic acid [ No CAS ]
(R)-tert-butyl (1-(4-(2-amino-1H-benzo[d]imidazol-4-yl)-2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenylsulfonamido)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/206101,2016,A1

33
[ 100927-10-4 ]
[ 82689-16-5 ]
C₂₇H₄₆N₄O₆ [ No CAS ]

Reference： [1]Patent: KR101898106,2018,B1 .Location in patent: Paragraph 0120; 0131

34
[ 100927-10-4 ]
[ 117241-33-5 ]
(R)-tert-butyl (1-(3,4,5-tris(dodecyloxy)benzamido)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019

35
[ 100927-10-4 ]
[ 79-04-9 ]
tert-butyl N-[(2R)-1-(2-chloroacetamido)propan-2-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; ethyl acetate; at 0 - 20℃; for 2.0h;	To a stirred solution of <strong>[100927-10-4]tert-butyl N-[(2R)-1-aminopropan-2-yl]carbamate</strong>(3 g, 17.217 mmol, 1 equiv.) in EA(50 mL) was added the solution of Na2CO3(3649.65 mg, 34.434 mmol, 2 equiv.) in H2O(10 mL) at room temperature.Then the solution of 2-chloroacetyl chloride(3.89 g, 34.434 mmol, 2 equiv.) in EA (10 mL) was added dropwise at 0 degrees C. The resulting mixture was stirred for 2 h at room temperature. The reaction was monitored by LCMS. The reaction was quenched with Water at room temperature. The resulting mixture was extracted with EtOAc (3 x 100 mL). The combined organic layers were washed with brine (1 x 100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. This resulted in tert-butyl N-[(2R)-1-(2-chloroacetamido)propan-2-yl]carbamate(4.5g,crude) as a white solid.

Reference： [1]Patent: WO2019/55966,2019,A2 .Location in patent: Page/Page column 373

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P321
P322
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P337	If eye irritation persists:
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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.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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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.
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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.
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P401
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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
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H226	Flammable liquid and vapour
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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. 100927-10-4 ] {[proInfo.proName]}

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[ 100927-10-4 ] Synthesis Path-Upstream 1~9

[ 100927-10-4 ] Synthesis Path-Downstream 1~35

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Aliphatic Chain Hydrocarbons

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