(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline → HCID 86751999, compound

HRID 727656Notes

Reaction equation

HRID 727656 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.[N+:32]([C:35]1[CH:63]=[CH:62][C:38]([CH2:39][O:40][C:41]([CH:43]2[CH2:48][NH:47][CH2:46][CH2:45][N:44]2[C:49]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][C:56]([N+:59]([O-:61])=[O:60])=[CH:55][CH:54]=2)=[O:50])=[O:42])=[CH:37][CH:36]=1)([O-:34])=[O:33]>>[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:47]2[CH2:46][CH2:45][N:44]([C:49]([O:51][CH2:52][C:53]3[CH:54]=[CH:55][C:56]([N+:59]([O-:61])=[O:60])=[CH:57][CH:58]=3)=[O:50])[CH:43]([C:41]([O:40][CH2:39][C:38]3[CH:62]=[CH:63][C:35]([N+:32]([O-:34])=[O:33])=[CH:36][CH:37]=3)=[O:42])[CH2:48]2)=[O:29])[CH2:10]1

Participants

3

Reactant 2

HCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 540916691,2-Bis[(4-nitrophenyl)methyl] 1,2-piperazinedicarboxylate

Product 1

HCID 86751999HCID 86751999, compoundYield 34.1%

Procedure

Following a procedure similar to that described in Preparation 8, but using 0.47 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 0.20 g of N,N'-carbonyldiimidazole and 0.70 g of 2-(4-nitrobenzyloxycarbonyl)-1-(4-nitrobenzyloxycarbonyl)piperazine, 270 mg of the title compound were obtained as an amorphous solid.

Workup

  1. customthat described in Preparation 8

Sources & evidence

ORD record
ord-28890f1e76c141aab4b2a0456120fe63
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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