(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidine → (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(3(allyloxycarbonylmethoxymethyl)phenylcarbamoyl)pyrrolidine

HRID 260317Notes

Reaction equation

HRID 260317 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][CH2:7][C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9].[C:17]([S:20][C@@H:21]1[CH2:25][N:24]([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])[C@H:23]([C:32](O)=[O:33])[CH2:22]1)(=[O:19])[CH3:18].NC1C=C(C=CC=1)OCC(OCC=C)=O>>[C:17]([S:20][C@@H:21]1[CH2:25][N:24]([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])[C@H:23]([C:32](=[O:33])[NH:1][C:2]2[CH:16]=[CH:15][CH:14]=[C:4]([CH2:5][O:6][CH2:7][C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])[CH:3]=2)[CH2:22]1)(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 15299255(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidineHCID 22401146Allyl 3-aminobenzyloxyacetateHCID 22401151Allyl 3-aminophenoxyacetate

Product 1

HCID 57141411(2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(3(allyloxycarbonylmethoxymethyl)phenylcarbamoyl)pyrrolidine

Procedure

Allyl 3-aminobenzyloxyacetate was condensed with (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidine by the method described in example 3 for allyl 3-aminophenoxyacetate, except that crude product was purified by chromatography on silica, using a gradient from di-chloromethane to dichloromethane/diethyl ether (85:15), to give (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(3(allyloxycarbonylmethoxymethyl)phenylcarbamoyl)pyrrolidine.

Workup

  1. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-362d96d2bdfb4c769a021b97d5f960d9
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

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