Acetonitrile → HCID 57524147, compound
Reaction equation
[C:1](#[N:3])[CH3:2].[Li]CCCC.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:23]2[C:31]3[C:26](=[C:27]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)([CH2:21][CH3:22])[C:17](OC)=[O:18])=[CH:12][CH:11]=1>O1CCCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:23]2[C:31]3[C:26](=[C:27]([NH:32][S:33]([CH3:36])(=[O:34])=[O:35])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)([CH2:21][CH3:22])[C:17](=[O:18])[CH2:2][C:1]#[N:3])=[CH:12][CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of acetonitrile (180 mg, 4.4 mmol) in tetrahydrofuran (3 mL) was added BuLi (1.9 mL, 4.8 mmol, 2.5 M in hexane) at −78° C. After stirring for 30 min, a solution of methyl 2-(4-chlorophenyl)-2-(4-(methylsulfonamido)-1H-indol-1-yl)butanoate (840 mg, 2.0 mmol, Enantiomer A), as described in Example 3 step D, in tetrahydrofuran (3 mL) was added to the mixture at −78° C. The resulting mixture was stirred at −78° C. for another 1 h, and then quenched with water (15 mL), extracted with ethyl acetate. The combined organics were washed with brine (15 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with PE/EA (5/1 to 3/1, v/v) to get the title compound as a colorless amorphous solid (Enantiomer A). LC/MS m/z=429.8[M+H]+.