Dichloromethane → (2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2(isopropylsulfinyl)ethyl]pyrrolidine

HRID 1720485Notes

Reaction equation

HRID 1720485 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]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 22860055(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(isopropylthio)ethyl]pyrrolidine

Product 1

HCID 57234092(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2(isopropylsulfinyl)ethyl]pyrrolidine

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.

Sources & evidence

ORD record
ord-50deca67cb5b48e8b914dc7ffb2cd490
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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