Ethylenediamine → (2S,4S)-4-Mercapto-2-(N-[2-(N-4-nitrobenzyloxycarbonylacetimidoyl)aminoethyl]carbamoyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 727658Notes

Reaction equation

HRID 727658 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.[CH2:32]([NH2:35])[CH2:33][NH2:34].[N+:36]([C:39]1[CH:52]=[CH:51][C:42]([CH2:43][O:44][C:45]([NH:47][C:48](=N)[CH3:49])=[O:46])=[CH:41][CH:40]=1)([O-:38])=[O:37]>>[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](=[O:29])[NH:34][CH2:33][CH2:32][NH:35][C:48](=[N:47][C:45]([O:44][CH2:43][C:42]2[CH:51]=[CH:52][C:39]([N+:36]([O-:38])=[O:37])=[CH:40][CH:41]=2)=[O:46])[CH3:49])[CH2:10]1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 140352007HCID 140352007, compound

Product 1

HCID 178465421(2S,4S)-4-Mercapto-2-(N-[2-(N-4-nitrobenzyloxycarbonylacetimidoyl)aminoethyl]carbamoyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 27.6%

Procedure

Following a procedure similar to that described in Preparation 17, but using 850 mg of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 450 mg of ethylenediamine and 430 mg of N-(4-nitrobenzyloxycarbonyl)acetamidine, 295 mg of the title compound were obtained as a powder.

Workup

  1. customthat described in Preparation 17

Sources & evidence

ORD record
ord-fdf6f1e4638b4865ad1c7cb5b1d9a6ee
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

Loading…