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

HRID 1720477Notes

Reaction equation

HRID 1720477 reaction equation
[OH:1][CH:2]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:34])[C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23](=[O:33])[CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:3][S:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].CS(C)=O.C1CCC(N=C=NC2CCCCC2)CC1>>[C:27]1([CH2:26][CH2:25][CH2:24][C:23]([N:19]2[CH2:20][CH2:21][CH2:22][C@H:18]2[C:17]([N:13]2[CH2:14][CH2:15][CH2:16][C@H:12]2[C:2](=[O:1])[CH2:3][S:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[O:34])=[O:33])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 70049848(2S)-2-[1-Hydroxy-2-(phenylsulfinyl)ethyl]-1-[N-(4-phenylbutyryl)-L-prolyl]pyrrolidineHCID 86749402Dmso dcc

Product 1

HCID 70049525(2S)-1-[N-(4-phenylbutyryl)-L-prolyl]-2-[(phenylsulfinyl)acetyl]-pyrrolidineYield 83.5%

Procedure

(2S)-2-[1-Hydroxy-2-(phenylsulfinyl)ethyl]-1-[N-(4-phenylbutyryl)-L-prolyl]pyrrolidine (1.07 g) was subjected to DMSO-DCC oxidation as in Example 1-D) to give 0.89 g of (2S)-1-[N-(4-phenylbutyryl)-L-prolyl]-2-[(phenylsulfinyl)acetyl]-pyrrolidine (See Table 2).

Sources & evidence

ORD record
ord-8a829cd8fcf7461d984fe0d81bc61a01
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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