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

HRID 1720471Notes

Reaction equation

HRID 1720471 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:34][CH2:33][CH2:32][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:31])[CH2:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[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[CH2:34][CH2:33][CH2:32][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:31])[CH2:21][S:22]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)(=[O:24])=[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 57008408(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(phenylsulfonyl)ethyl]pyrrolidineHCID 86749402Dmso dcc

Product 1

HCID 15297818(2S)-1-(N-benzyloxycarbonyl-L-prolyl)-2-[(phenylsulfonyl)acetyl]-pyrrolidineYield 82.7%

Procedure

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(phenylsulfonyl)ethyl]pyrrolidine (500 mg) was subjected to DMSO-DCC oxidation as in Example 1-D) to give 412 mg of (2S)-1-(N-benzyloxycarbonyl-L-prolyl)-2-[(phenylsulfonyl)acetyl]-pyrrolidine (See Table 1).

Sources & evidence

ORD record
ord-594f2f2101c24a9bb079d6917c41c8e8
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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