(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline → HCID 86751993, compound

HRID 727634Notes

Reaction equation

HRID 727634 reaction equation
COC1C=CC(C[S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27]([OH:29])=O)[CH2:10]2)=CC=1.[CH3:32][C@@H:33]1[CH2:38][NH:37][CH2:36][CH2:35][N:34]1[C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][CH:44]=1)=[O:40]>>[SH:8][C@@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)=[O:15])[C@H:11]([C:27]([N:37]2[CH2:36][CH2:35][N:34]([C:39]([O:41][CH2:42][C:43]3[CH:44]=[CH:45][C:46]([N+:49]([O-:51])=[O:50])=[CH:47][CH:48]=3)=[O:40])[C@H:33]([CH3:32])[CH2:38]2)=[O:29])[CH2:10]1

Participants

3

Reactant 2

HCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 54353395HCID 54353395, compound

Product 1

HCID 86751993HCID 86751993, compoundYield 69.4%

Procedure

Following a procedure similar to that described in Preparation 8, but using 0.23 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 0.10 g of N,N'-carbonyldiimidazole and 0.17 g of (2R)-2-methyl-1-(4-nitrobenzyloxycarbonyl)piperazine, 0.21 g of the title compound was obtained as an amorphous solid.

Workup

  1. customthat described in Preparation 8

Sources & evidence

ORD record
ord-2ef3c962064d4f3eae06d6a074919489
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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