(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine → (2S)-1-(N-benzyloxycarbonyl-L-prolyl)-2-(phenoxyacetyl)-pyrrolidine

HRID 1720473Notes

Reaction equation

HRID 1720473 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:32][CH2:31][CH2:30][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[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[CH2:32][CH2:31][CH2:30][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 57049295(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-(1-hydroxy-2-phenoxyethyl)pyrrolidineHCID 86749402Dmso dcc

Product 1

HCID 15297819(2S)-1-(N-benzyloxycarbonyl-L-prolyl)-2-(phenoxyacetyl)-pyrrolidineYield 83.8%

Procedure

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine (393 mg) was subjected to DMSO-DCC oxidation in the same manner as in Example 1-D) to give 328 mg of (2S)-1-(N-benzyloxycarbonyl-L-prolyl)-2-(phenoxyacetyl)-pyrrolidine (See Table 2).

Sources & evidence

ORD record
ord-5192bc4a33cf4df0856edccb8576672e
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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