Dichloromethane → (2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2(isopropylsulfinyl)ethyl]pyrrolidine
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:29][CH2:28][CH2:27][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:26])[CH2:21][S:22][CH:23]([CH3:25])[CH3:24])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:41])C=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:29][CH2:28][CH2:27][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:26])[CH2:21][S:22]([CH:23]([CH3:24])[CH3:25])=[O:41])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(isopropylthio)ethyl]pyrrolidine (1.61 g) was subjected to oxidation as in Example 2-A) in dichloromethane using 1.1 equivalent of m-chloroperbenzoic acid to give 1.40 g of the title compound.