(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(4-nitrophenylsulfinyl)ethyl]pyrrolidine → (2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[(4-nitrophenylsulfinyl)acetyl]pyrrolidine

HRID 1720483Notes

Reaction equation

HRID 1720483 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:36][CH2:35][CH2:34][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:33])[CH2:21][S:22]([C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:23])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.C1CCC(N=C=NC2CCCCC2)CC1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:36][CH2:35][CH2:34][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:33])[CH2:21][S:22]([C:24]1[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=1)=[O:23])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 56997501(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(4-nitrophenylsulfinyl)ethyl]pyrrolidineHCID 86749402Dmso dcc

Product 1

HCID 57138399(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[(4-nitrophenylsulfinyl)acetyl]pyrrolidineYield 76.5%

Procedure

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(4-nitrophenylsulfinyl)ethyl]pyrrolidine (883 mg) was subjected to DMSO-DCC oxidation as in Example 1-D) to give 673 mg of the title compound (See Table 3).

Sources & evidence

ORD record
ord-1bbc771c5caa4b0687d801183794398f
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

Loading…