Name: 37592-53-3|(S)-Isopropyl 2-amino-3-hydroxypropanoate hydrochloride|97%
Brand: Ambeed
SKU: A802373
Price: 11.0 USD
Availability: InStock
Rating: 93 (32 reviews)

1
[ 14389-86-7 ]
[ 37592-53-3 ]
[ 84028-52-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; dicyclohexyl-carbodiimide In dichloromethane 1.) 0 deg C, 1 h, 2.) RT 3 h;

Reference： [1]Maurer, Peter J.; Miller, Marvin J. [Journal of the American Chemical Society, 1983, vol. 105, # 2, p. 240 - 245]

2
[ 5333-86-8 ]
[ 37592-53-3 ]
[ 609366-73-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: L-serine isopropyl ester hydrochloride With triethylamine In chloroform at 20℃; Stage #2: ethyl benzimidate hydrochloride In chloroform for 24h; Heating;

Reference： [1]Meyer, Franck; Laaziri, Abdelhamid; Papini, Anna Maria; Uziel, Jacques; Juge, Sylvain [Tetrahedron Asymmetry, 2003, vol. 14, # 15, p. 2229 - 2238]

3
Ethyl 3-amino-3-ethoxyprop-2-enimidate dihydrochloride [ No CAS ]
[ 37592-53-3 ]
(S,S)-2,2'-methylenebis(4-isopropoxycarbonyl-2-oxazoline) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With triethylamine In acetonitrile at 20℃; for 72h;

Reference： [1]Matsumoto, Kenji; Jitsukawa, Koichiro; Masuda, Hideki [Tetrahedron Letters, 2005, vol. 46, # 34, p. 5687 - 5690]

4
[ 13734-41-3 ]
[ 37592-53-3 ]
[ 1245542-46-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Location in patent: experimental part Krečmerová, Marcela; Holý, Antonín; Andrei, Graciela; Pomeisl, Karel; Tichý, Tomáš; Břehová, Petra; Masojídková, Milena; Dračínský, Martin; Pohl, Radek; Laflamme, Genevieve; Naesens, Lieve; Hui, Hon; Cihlar, Tomas; Neyts, Johan; De Clercq, Erik; Balzarini, Jan; Snoeck, Robert [Journal of Medicinal Chemistry, 2010, vol. 53, # 19, p. 6825 - 6837]

5
[ 56-45-1 ]
[ 67-63-0 ]
[ 37592-53-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride at 0℃; for 8h; Schlenk technique; Reflux;
87%	With chloro-trimethyl-silane for 5h; Reflux;
80%	With thionyl chloride at 0 - 20℃; for 17h;

	With thionyl chloride at 0℃; Reflux;	4.3. General procedure for the synthesis of l-serine ester (10a-e) General procedure: To a solution of l-serine (1 equiv.) in alcohol reagent (methanol, ethanol, propanol, isopropanol or isobutanol) was added dropwise thionyl chloride (3 equiv.) at less then 0 °C using a salted ice bath. The mixture was heated under reflux for 2-10 h. The reaction mixture was then concentrated under reduced pressure to yield a white solid.
	With thionyl chloride at 0℃; Reflux;	4.9. General procedure for the synthesis of l-serine ester (11a-b) General procedure: To a solution of L-serine (1 equiv.) in alcohol reagent (isopropanolor isobutanol), cooled to <0 C, was added dropwise thionylchloride (3 equiv.). The mixture was heated under reflux for 6h. The reaction mixture was then concentrated under reduced pressure to yield a white solid.
	With thionyl chloride at 0℃; Reflux;	General procedure for the synthesis of L-serineester (10a-b) General procedure: To asolution of L-serine (1 equiv.)in alcoholreagent (isopropanolorisobutanol) was addeddropwise thionyl chloride (3 equiv.)atless than 0 °Cusing a salted ice bath. The mixture was heated under reflux for 2-10 h.The reaction mixture was then concentrated under reduced pressure to yield a white solid.

Reference： [1]Biancalana, Lorenzo; Bortoluzzi, Marco; Ferretti, Eleonora; Hayatifar, Mohammad; Marchetti, Fabio; Pampaloni, Guido; Zacchini, Stefano [RSC Advances, 2017, vol. 7, # 17, p. 10158 - 10174]
[2]Location in patent: experimental part Peterson, Larryn W.; Sala-Rabanal, Monica; Krylov, Ivan S.; Serpi, Michaela; Kashemirov, Boris A.; McKenna, Charles E. [Molecular Pharmaceutics, 2010, vol. 7, # 6, p. 2349 - 2361]
[3]Location in patent: experimental part van Dijk, Maarten; Postma, Tobias M.; Rijkers, Dirk T.S.; Liskamp, Rob M.J.; van Nostrum, Cornelus F.; Hennink, Wim E. [Polymer, 2010, vol. 51, # 12, p. 2479 - 2485]
[4]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]
[5]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]
[6]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

6
[ 24424-99-5 ]
[ 37592-53-3 ]
[ 1253690-12-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In acetonitrile at 20℃; for 1h;

Reference： [1]Location in patent: experimental part Peterson, Larryn W.; Sala-Rabanal, Monica; Krylov, Ivan S.; Serpi, Michaela; Kashemirov, Boris A.; McKenna, Charles E. [Molecular Pharmaceutics, 2010, vol. 7, # 6, p. 2349 - 2361]

7
[ 37592-53-3 ]
[ 18162-48-6 ]
[ 1254155-99-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1H-imidazole In dichloromethane at 0 - 20℃; for 24h;

Reference： [1]Location in patent: experimental part Peterson, Larryn W.; Sala-Rabanal, Monica; Krylov, Ivan S.; Serpi, Michaela; Kashemirov, Boris A.; McKenna, Charles E. [Molecular Pharmaceutics, 2010, vol. 7, # 6, p. 2349 - 2361]

8
[ 37592-53-3 ]
[ 920-46-7 ]
[ 1235740-13-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In 1,4-dioxane; water at 0 - 20℃; for 16h;

Reference： [1]Location in patent: experimental part van Dijk, Maarten; Postma, Tobias M.; Rijkers, Dirk T.S.; Liskamp, Rob M.J.; van Nostrum, Cornelus F.; Hennink, Wim E. [Polymer, 2010, vol. 51, # 12, p. 2479 - 2485]

9
[ 37592-53-3 ]
[ 92-92-2 ]
C₁₉H₂₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: biphenyl-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

10
[ 365-12-8 ]
[ 37592-53-3 ]
C₁₉H₂₀FNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2'-fluorobiphenyl-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

11
[ 365-12-8 ]
[ 37592-53-3 ]
(S)-2-(2'-fluoro-1,1'-biphenyl-4-carboxamido)-3-(1H-imidazol-1-yl)propionic acid isopropyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C 1.2: 70 °C 2.1: 1,1'-carbonyldiimidazole / acetonitrile / Reflux

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

12
[ 3808-93-3 ]
[ 37592-53-3 ]
C₁₉H₂₀ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2'-chloro[1,1'-biphenyl]-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

13
[ 3808-93-3 ]
[ 37592-53-3 ]
isopropyl (S)-2-(2'-chloro-[1,1'-biphenyl]-4-carboxamido)-3-(1H-imidazol-1-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C 1.2: 70 °C 2.1: 1,1'-carbonyldiimidazole / acetonitrile / Reflux

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

14
[ 5748-43-6 ]
[ 37592-53-3 ]
C₂₀H₂₃NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(2-methylphenyl)benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

15
[ 5731-10-2 ]
[ 37592-53-3 ]
C₁₉H₂₀FNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4'-fluoro-biphenyl-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

16
[ 5748-41-4 ]
[ 37592-53-3 ]
C₁₉H₂₀ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 750 - 758

17
[ 5748-41-4 ]
[ 37592-53-3 ]
isopropyl (S)-2-(4'-chloro-[1,1'-biphenyl]-4-carboxamido)-3-(1H-imidazol-1-yl)propanoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 750 - 758

18
[ 720-73-0 ]
[ 37592-53-3 ]
C₂₀H₂₃NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4'-methyl-biphenyl-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

19
[ 728919-11-7 ]
[ 37592-53-3 ]
C₂₀H₂₀F₃NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(4-(trifluoromethoxy)phenyl)benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

20
[ 37592-53-3 ]
[ 195457-71-7 ]
C₂₀H₂₀F₃NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 750 - 758

21
[ 37592-53-3 ]
[ 195457-71-7 ]
isopropyl (S)-3-(1H-imidazol-1-yl)-2-(4'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxamido)propanoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 750 - 758

22
[ 1841-58-3 ]
[ 37592-53-3 ]
C₁₉H₂₀FNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3′-fluoro-(1,1′-biphenyl)-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

23
[ 37592-53-3 ]
[ 331760-41-9 ]
C₁₉H₁₉F₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2',4'-difluoro-biphenyl-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

24
[ 505082-81-5 ]
[ 37592-53-3 ]
C₁₉H₁₉F₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3',4'-difluoro-biphenyl-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

25
C₁₃H₈F₂O₂ [ No CAS ]
[ 37592-53-3 ]
C₁₉H₁₉F₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₃H₈F₂O₂ With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	4.4. General procedure for the synthesis of compounds (11a-v) General procedure: To a solution of the intermediate acid compound (1 equiv.) in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1 equiv), respectively. The reaction mixture was stirred for 2 h at ambient temperature, and the l-serine ester (1.1 equiv.) and DIEA (3 equiv.) were added. The solution was heated to 70 °C for 6 h and then cooled to room temperature. The reaction mixture was poured into ice water, the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Dongmei; Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Liu, Chunchi; Hao, Chenzhou; Sun, Bin; Su, Xin; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758]

26
[ 37592-53-3 ]
[ 53517-65-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydroxide In dichloromethane at 20℃; for 0.166667h;

Reference： [1]Biancalana, Lorenzo; Bortoluzzi, Marco; Ferretti, Eleonora; Hayatifar, Mohammad; Marchetti, Fabio; Pampaloni, Guido; Zacchini, Stefano [RSC Advances, 2017, vol. 7, # 17, p. 10158 - 10174]

27
5-[[4-chloro-5-[(1S)-4-(2-fluorophenyl)indan-1-yl]oxy-2-formylphenoxy]methyl]pyridine-3-carbonitrile [ No CAS ]
[ 37592-53-3 ]
1-methylethyl (2S)-2-[[5-chloro-2-[(5-cyano-3-pyridyl)methoxy]-4-[(1S)-4-(2-fluorophenyl)indan-1-yl]oxy-phenyl]methylamino]-3-hydroxypropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 50℃; for 0.333333h;	19 Example 19 Synthesis of 1-methylethyl (2S)-2-[[5-chloro-2-[(5-cyano-3-pyridyl)methoxy]-4-[(1S)-4-(2-fluorophenyl)indan-1-yl]oxy-phenyl]methylamino]-3-hydroxy-propanoate To a solution of 5-[[4-chloro-5-[(1S)-4-(2-fluorophenyl)indan-1-yl]oxy-2-formyl-phenoxy]methyl]pyridine-3-carbonitrile (67 mg, 0.13 mmol) in NMP (1 mL) was added L-serine isopropyl ester hydrochloride (110 mg, 0.59 mmol, prepared according to the procedure in J. Med. Chem. 53(19), 6625-6837; 2010), N-ethyl-N-(propan-2-yl))propan-2-amine (0.09 mL, 0.50 mmol), Na(OAc)3BH (100 mg, 0.49 mmol) and acetic acid (0.10 mL, 1.8 mmol). The resulting suspension was stirred at 50° C. for 20 minutes. The reaction mixture was diluted with 2:1 CHCl3/i-PrOH (5 mL), washed with water (1 mL), and concentrated in vacuo. The crude residue was purified by reverse phase preparative HPLC (CH3CN-H2O with 0.1% TFA) to obtain 1-methylethyl (2S)-2-[[5-chloro-2-[(5-cyano-3-pyridyl)methoxy]-4-[(1S)-4-(2-fluorophenyl)indan-1-yl]oxy-phenyl]methylamino]-3-hydroxy-propanoate as a trifluoroacetic acid salt. The salt was neutralized by passing the purified fractions through an Agilent Technologies PL-HCO3 MP SPE cartridge to obtain the neutral form. dr: ˜3.5:1. MS: (ES) m/z calculated for C35H33ClFN3O5 [M+H]+ 630.2. found 630.2. 1H NMR (400 MHz, Methanol-d) δ 8.97 (d, J=2.2 Hz 1H), 8.92 (d, J=2.0 Hz, 1H), 8.51 (s, 1H), 7.47 (s, 1H), 7.45-7.17 (m, 7H), 7.08 (s, 1H), 6.04-5.99 (m, 1H), 5.37 (s, 2H), 5.06 (m, 1H), 4.24-4.13 (m, 2H), 3.97-3.85 (m, 3H), 3.09-2.98 (m, 1H), 2.88-2.78 (m, 1H), 2.62-2.53 (m, 1H), 2.20-2.10 (m, 1H), 1.29-1.22 (m, 6H).

Reference： [1]Current Patent Assignee: CHEMOCENTRYX INC - US2018/8554, 2018, A1 Location in patent: Paragraph 0251; 0252

28
[ 154235-77-5 ]
[ 37592-53-3 ]
isopropyl (S)-2-(benzo[d]oxazole-6-carboxamido)-3-(1H-imidazol-1-yl)propanoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3242 - 3253

29
[ 154235-77-5 ]
[ 37592-53-3 ]
C₁₄H₁₆N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3242 - 3253

30
[ 37592-53-3 ]
[ 13452-14-7 ]
isopropyl (S)-3-(1H-imidazol-1-yl)-2-(2-methylbenzo[d]oxazole-6-carboxamido)propanoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3242 - 3253

31
[ 37592-53-3 ]
[ 13452-14-7 ]
C₁₅H₁₈N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3242 - 3253

32
[ 6314-28-9 ]
[ 37592-53-3 ]
C₁₅H₁₇NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: benzo[b]thiophene-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	4.10. General procedure for the synthesis of compounds (12a-t) General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]

33
[ 496-41-3 ]
[ 37592-53-3 ]
C₁₅H₁₇NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Benzofuran-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	4.10. General procedure for the synthesis of compounds (12a-t) General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]

34
[ 6480-68-8 ]
[ 37592-53-3 ]
C₁₆H₁₈N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: quinoline-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	4.10. General procedure for the synthesis of compounds (12a-t) General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]

35
[ 37592-53-3 ]
[ 879-65-2 ]
C₁₅H₁₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3242 - 3253

36
[ 3093-97-8 ]
[ 37592-53-3 ]
C₁₅H₁₇FN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3242 - 3253

37
[ 37592-53-3 ]
[ 16136-58-6 ]
C₁₆H₂₀N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-methyl-1H-indole-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	4.10. General procedure for the synthesis of compounds (12a-t) General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]

38
[ 2849-93-6 ]
[ 37592-53-3 ]
C₁₄H₁₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-benzimidazolecarboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	4.10. General procedure for the synthesis of compounds (12a-t) General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]

39
[ 94-53-1 ]
[ 37592-53-3 ]
C₁₄H₁₇NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Piperonylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	4.10. General procedure for the synthesis of compounds (12a-t) General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]

40
[ 37592-53-3 ]
[ 26664-02-8 ]
C₁₈H₂₀N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	4.10. General procedure for the synthesis of compounds (12a-t) General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]

41
C₁₃H₁₁NO₃ [ No CAS ]
[ 37592-53-3 ]
C₁₉H₂₂N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₃H₁₁NO₃ With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	4.10. General procedure for the synthesis of compounds (12a-t) General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

Reference： [1]Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253]

42
[ 69240-50-2 ]
[ 37592-53-3 ]
isopropyl (S)-3-(1H-imidazol-1-yl)-2-(3-methyl-[1,1'-biphenyl]-4-carboxamido)propanoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2448 - 2451

43
[ 69240-50-2 ]
[ 37592-53-3 ]
C₂₀H₂₃NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2448 - 2451

44
[ 175153-18-1 ]
[ 37592-53-3 ]
C₂₀H₂₃NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-(methyloxy)-4-biphenylcarboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

45
[ 5728-41-6 ]
[ 37592-53-3 ]
C₁₉H₂₀ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-chlorobiphenyl-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

46
[ 178313-67-2 ]
[ 37592-53-3 ]
C₂₀H₂₃NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-methyl[1,1'-biphenyl]-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

47
[ 505083-02-3 ]
[ 37592-53-3 ]
C₁₉H₁₉F₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-phenyl-2,6-difluorobenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

48
[ 5728-40-5 ]
[ 37592-53-3 ]
isopropyl (S)-2-(3-chloro-[1,1'-biphenyl]-4-carboxamido)-3-(1H-imidazol-1-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 2 h / 20 °C 1.2: 6 h / 70 °C 2.1: acetonitrile / 6 h / Reflux

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

49
[ 5728-40-5 ]
[ 37592-53-3 ]
C₁₉H₂₀ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-chloro-[1,1'-biphenyl]-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

50
[ 137045-30-8 ]
[ 37592-53-3 ]
isopropyl (S)-2-(2-fluoro-[1,1'-biphenyl]-4-carboxamido)-3-(1H-imidazol-1-yl)propanoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2448 - 2451

51
[ 137045-30-8 ]
[ 37592-53-3 ]
C₁₉H₂₀FNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2448 - 2451

52
[ 37592-53-3 ]
3-fluoro-[1,1'-biphenyl]-4-carboxylic acid [ No CAS ]
C₁₉H₂₀FNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-fluoro-[1,1'-biphenyl]-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

53
C₁₄H₈FNO₂ [ No CAS ]
[ 37592-53-3 ]
C₂₀H₁₉FN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₄H₈FNO₂ With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

54
[ 505082-83-7 ]
[ 37592-53-3 ]
C₁₉H₁₉F₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2',3-difluoro-[1,1'-biphenyl]-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

55
[ 1192548-50-7 ]
[ 37592-53-3 ]
C₁₉H₁₉F₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₃H₈F₂O₂ With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: L-serine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 6h;	General procedure for the synthesis ofcompounds (11a-v) General procedure: To a solution of the intermediateacid compound (1 equiv.) in anhydrous DMF was added EDCI(1.1 equiv) and HOBt(1.1equiv), respectively. The reaction mixture was stirredfor 2 h atambient temperature, and the L-serine ester (1.1 equiv.) and DIEA (3 equiv.)were added. The solution was heated to 70 °Cfor 6 h and then cooled to room temperature. The reaction mixture was pouredinto ice water,the resulting solidwas filtered and dried to give the desiredcompound.

Reference： [1]Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Wei, Peng; Wu, Mengya; Su, Xin; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 17, p. 2448 - 2451]

56
2-(pyridin-3-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzaldehyde [ No CAS ]
[ 37592-53-3 ]
(S)-N-(2-(pyridin-3-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzyl)serine isopropyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
328 mg	Stage #1: 2-(pyridin-3-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzaldehyde; L-serine isopropyl ester hydrochloride With acetic acid In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: With sodium cyanoborohydride In N,N-dimethyl-formamide at 25℃;	1 (S)-N-(2-(pyridine-3-methoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzyl)serine isopropyl ester Weigh out 2-(pyridine-3-methoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzaldehyde (600mg, 1mmol) in 10ml DMF, add L-serine isopropyl ester hydrochloride (367mg, 2mmol), glacial acetic acid (180mg, 3mmol) was added dropwise to the reaction system, After stirring for 20 min at room temperature, sodium cyanoborohydride (126 mg, 2 mmol) was added and reacted overnight at 25°C. Stop the reaction, add water and ethyl acetate to extract and separate the liquid 3 times,The organic phase was washed with saturated brine, dried with anhydrous sodium sulfate, filtered, evaporate to dryness under reduced pressure and separate by silica gel column chromatography to obtain the nitrogen boron complex as a colorless oil (TLC shows that the product is very few, most of which are nitrogen boron complex), the nitrogen boron complex was refluxed with 30 ml isopropanol for 12 hours, and silica gel column chromatography was used to obtain 328 mg of colorless oil.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN111662270, 2020, A Location in patent: Paragraph 0273-0274; 0277-0278

57
2-(2-cyanopyridin-4-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzaldehyde [ No CAS ]
[ 37592-53-3 ]
(S)-N-(2-(2-cyanopyridin-4-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzyl)serine isopropyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48 mg	Stage #1: 2-(2-cyanopyridin-4-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzaldehyde; L-serine isopropyl ester hydrochloride With acetic acid In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With sodium cyanoborohydride In N,N-dimethyl-formamide at 20℃; for 2h;	3 (S)-N-(2-(2-cyanopyridine-4-methoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzyl)serine isopropyl ester Weigh out 2-(2-cyanopyridine-4-methoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-iodobenzaldehyde (100mg, 0.161mmol) and dissolve it in 5ml DMF, L-serine isopropyl ester hydrochloride (59mg, 0.321mmol) was added, and glacial acetic acid (58mg, 0.963mmol) was added dropwise to the reaction system. After stirring for 30min at room temperature, sodium cyanoborohydride (21mg, 0.321mmol) was added. ), after reacting at room temperature for 2h, TLC showed that the reaction of the raw materials was basically complete, the reaction was stopped, water and ethyl acetate were added to extract the liquid *3, and the organic phase was washed with saturated brine. It was dried over anhydrous sodium sulfate, filtered, evaporated to dryness under reduced pressure, and passed through silica gel column chromatography (DCM--DCM:MeOH=100:1---40:1---20:1) to obtain 48 mg of off-white solid.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN111662270, 2020, A Location in patent: Paragraph 0282-0283; 0286-0287

58
2-(pyridin-3-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzaldehyde [ No CAS ]
[ 37592-53-3 ]
(S)-N-(2-(pyridin-3-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzyl)serine isopropyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(pyridin-3-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzaldehyde; L-serine isopropyl ester hydrochloride With acetic acid In isopropyl alcohol at 20℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In isopropyl alcohol at 20℃; for 12h;	4 (S)-N-(2-(pyridine-3-methoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzyl)serine isopropyl ester: Weigh out 2-(pyridine-3-methoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzaldehyde (300mg, 0.471mmol) and dissolve it in 5-8ml isopropanol, add L-serine isopropyl ester hydrochloride (130mg, 0.706mmol), 0.1ml glacial acetic acid, after stirring for 30min at room temperature, Add sodium triacetoxyborohydride (198mg, 0.942mmol), After reacting at room temperature for 12 hours, add water and ethyl acetate to extract and separate three times. The organic phase was washed with saturated brine, dried with anhydrous sodium sulfate, filtered, Evaporate to dryness under reduced pressure and pass C-18 reverse phase silica gel column chromatography to obtain a colorless oil.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN111662270, 2020, A Location in patent: Paragraph 0288-0289; 0292-0293

59
2-(2-cyanopyridin-4-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzaldehyde [ No CAS ]
[ 37592-53-3 ]
(S)-N-(2-(2-cyanopyridin-4-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzyl)serine isopropyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35 mg	Stage #1: 2-(2-cyanopyridin-4-ylmethoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzaldehyde; L-serine isopropyl ester hydrochloride With acetic acid In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl-formamide at 20℃; for 1.5h;	6 (S)-N-(2-(2-cyanopyridine-4-methoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzyl)serine isopropyl ester: Weigh out 2-(2-cyanopyridine-4-methoxy)-4-(2-bromo-3-phenylbenzyloxy)-5-(trimethylstannyl)benzaldehyde (90mg, 0.136mmol), Dissolve in 5ml DMF, add L-serine isopropyl ester hydrochloride (50mg, 0.272mmol), glacial acetic acid (24mg, 0.408mmol), after stirring for 30 min at room temperature, sodium triacetoxyborohydride (17 mg, 0.272 mmol) was added and reacted at room temperature for 1.5 hours. TLC detects that the reaction is complete, add water and ethyl acetate to extract and separate 3 times, The organic phase was washed with saturated brine, dried with anhydrous sodium sulfate, filtered, It was evaporated to dryness under reduced pressure, and 70 mg of pale yellow oil was obtained by silica gel column chromatography. Semi-prepared by HPLC (condition: isocratic elution: 95% methanol/5% water), 35 mg of colorless oil is obtained.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN111662270, 2020, A Location in patent: Paragraph 0300-0301;

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	37592-53-3	MDL No. :	MFCD31630717
Formula :	C₆H₁₄ClNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZQSBPSWEMOKULO-JEDNCBNOSA-N
M.W :	183.63	Pubchem ID :	73947482
Synonyms :	L-Serine isopropyl ester hydrochloride	Chemical Name :	(S)-Isopropyl 2-amino-3-hydroxypropanoate hydrochloride

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	43.08
TPSA :	72.55 Å²

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) :	-7.31 cm/s

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.16
Log Po/w (WLOGP) :	0.06
Log Po/w (MLOGP) :	-0.11
Log Po/w (SILICOS-IT) :	-0.51
Consensus Log Po/w :	-0.08

[ CAS No. 37592-53-3 ] {[proInfo.proName]}

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[ 37592-53-3 ] Synthesis Path-Downstream 1~59

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[ 37592-53-3 ]

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

Log S (ESOL) :	-0.82
Solubility :	28.1 mg/ml ; 0.153 mol/l
Class :	Very soluble
Log S (Ali) :	-1.24
Solubility :	10.5 mg/ml ; 0.0574 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.11
Solubility :	236.0 mg/ml ; 1.29 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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

[ CAS No. 37592-53-3 ] {[proInfo.proName]}

Quality Control of [ 37592-53-3 ]

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[ 37592-53-3 ] Synthesis Path-Downstream 1~59

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[ 37592-53-3 ]