m-Chloroperbenzoic acid → (2S)-2-[1-Hydroxy-2-(phenylsulfinyl)ethyl]-1-[N-(4-phenylbutyryl)-L-prolyl]pyrrolidine

HRID 1720476Notes

Reaction equation

HRID 1720476 reaction equation
[OH:1][CH:2]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:33])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:32])[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:42])C=1>ClCCl>[OH:1][CH:2]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:33])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:32])[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][S:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:42]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70048625(2S)-2-[1-Hydroxy-2-(phenylthio)ethyl]-1-[N-(4-phenyl-butyryl)-L-prolyl]pyrrolidine

Product 1

HCID 70049848(2S)-2-[1-Hydroxy-2-(phenylsulfinyl)ethyl]-1-[N-(4-phenylbutyryl)-L-prolyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S)-2-[1-Hydroxy-2-(phenylthio)ethyl]-1-[N-(4-phenyl-butyryl)-L-prolyl]pyrrolidine (1.25 g) was subjected to oxidation in the same manner as in Example 2-A) in dichloromethane (9 ml) using 1.1 equivalent of m-chloroperbenzoic acid to give 1.18 g of (2S)-2-[1-hydroxy-2-(phenylsulfinyl)ethyl]-1-[N-(4-phenylbutyryl)-L-prolyl]-pyrrolidine.

Sources & evidence

ORD record
ord-81df56d206034e69957b1466af20c8ac
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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