Chlorotrimethylsilane → Methyl (S)-2-benzyloxycarbonylamino-4,4-difluoro-5-phenylpentanoate
Reaction equation
[CH3:1][Si](Cl)(C)C.[CH2:6]([O:13][C:14]([NH:16][C@@H:17]([CH2:21][C:22]([F:31])([F:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]([OH:20])=[O:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO>[CH2:6]([O:13][C:14]([NH:16][C@@H:17]([CH2:21][C:22]([F:30])([F:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]([O:20][CH3:1])=[O:19])=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Participants
4
Procedure
Trimethylsilyl chloride (0.61 g, 5.61 mmol, 2 eq) was added dropwise to a solution of (S)-2-benzyloxycarbonylamino-4,4-difluoro-5-phenylpentanoic acid (1.02 g, 2.81 mmol) in 40 ml of methanol. After the addition had ended, the mixture was stirred at RT for 3 h. The solvent was removed under reduced pressure and the residue was used crude in the reaction which followed.