ChemicalBook CAS DataBase List Daclatasvir Impurity F

Daclatasvir Impurity F synthesis

9synthesis methods

Product Name:Daclatasvir Impurity F
CAS Number:1007884-60-7
Molecular formula:C33H39N7O3
Molecular Weight:581.71

1-Pyrrolidinecarboxylic acid, 2-[5-[4'-[2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-2-pyrrolidinyl]-1H-imidazol-5-yl][1,1'-biphenyl]-4-yl]-1H-imidazol-2-yl]-, 1,1-dimethylethyl ester, (2S)-

1007884-59-4
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1007884-60-7
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Yield:1007884-60-7 96%

Reaction Conditions:

with trifluoroacetic acid in dichloromethane at 20; for 26 h;

Steps:

Methyl N-[(2S)-3-methyl-1-oxo-1-[(2S)-2-{5-[4-(4-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]butan-2-yl]carbamate (30)

To a solution containing the carbamate 29 (1.68 g, 2.46 mmol), 25% TFA/CH2Cl2 (12 mL) was added, and the resultant solution was stirred at ambient temperature for 26 h. The volatile component was removed under vacuum and the residue was free-based using two 6 g MCX cartridges (MeOH wash; 2.0 M NH3/MeOH elution) to afford 30 as a yellow foam (1.37 g, 96%).

References:

Li, Wenying;Zhao, Weiping;Liu, Xiaohong;Huang, Xiaohua;Lopez, Omar D.;Leet, John E.;Fancher, R. Marcus;Nguyen, Van;Goodrich, Jason;Easter, John;Hong, Yang;Caceres-Cortes, Janet;Chang, Shu Y.;Ma, Li;Belema, Makonen;Hamann, Lawrence G.;Gao, Min;Zhu, Mingshe;Shu, Yue-Zhong;Humphreys, W. Griffith;Johnson, Benjamin M. [Drug Metabolism and Disposition,2016,vol. 44,# 6,p. 809 - 820] Location in patent:supporting information