Acetyl chloride → HCID 14978405, compound

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:19])([C@@H:16]([SH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>ClCCl>[C:27]([S:18][C@@H:16]([CH3:17])[C@@:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([OH:19])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)(=[O:29])[CH3:28]

Participants

Procedure

To dichloromethane (1 ml) was added (2S,3S)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol (3 mg), followed by addition of a dichloromethane solution of triethylamine (10%, 16 μl) with ice-cooling. Then, a dichloromethane solution of acetyl chloride (10%, 8.2 μl) was added and the mixture was stirred at room temperature for 30 minutes. The solvent was then distilled off under reduced pressure and the residue was subjected to silica gel chromatography (1×1 cm) using ethyl acetate-hexane (2:1) as the eluent. The desired fraction was concentrated to give (2S,3S)-3-acetylthio-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (compound 44:1.2 mg) as a colorless solid.