(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline → HCID 22881635, compound

HRID 727650Notes

Reaction equation

HRID 727650 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.[C:32]([CH:35]1[CH2:40][NH:39][CH2:38][CH2:37][N:36]1[C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=1)=[O:42])(=[O:34])[NH2:33]>>[C:32]([CH:35]1[N:36]([C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=2)=[O:42])[CH2:37][CH2:38][N:39]([C:27]([C@@H:11]2[CH2:10][C@H:9]([SH:8])[CH2:13][N:12]2[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])=[O:29])[CH2:40]1)(=[O:34])[NH2:33]

Participants

3

Reactant 2

HCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 19704860(4-Nitrophenyl)methyl 2-(aminocarbonyl)-1-piperazinecarboxylate

Product 1

HCID 22881635HCID 22881635, compoundYield 70.7%

Procedure

Following a procedure similar to that described in Preparation 8, but using 2.18 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 0.79 g of N,N'-carbonyldiimidazole and 1.81 g of 2-carbamoyl-1-(4-nitrobenzyloxycarbonyl)piperazine, 2.13 g of the title compound were obtained as an amorphous solid.

Workup

  1. customthat described in Preparation 8

Sources & evidence

ORD record
ord-2aa8684342314da498acb87915f85d23
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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