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

HRID 1720494Notes

Reaction equation

HRID 1720494 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][O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[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][O:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 57161012(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[l-hydroxy-2-(4-methoxyphenoxy)ethyl]pyrrolidineHCID 86749402Dmso dcc

Product 1

HCID 70049382(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[(4-methoxyphenoxy)-acetyl]pyrrolidineYield 99%

Procedure

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[l-hydroxy-2-(4-methoxyphenoxy)ethyl]pyrrolidine (10.94 g) was subjected to DMSO-DCC oxidation in the same manner as in Example 1, D) to give 10.78 g of the title compound (See Table 6).

Sources & evidence

ORD record
ord-b6ae45869af84dd29b8b3c65e4c310ee
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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