(2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-[(3R)-pyrrolidin-3-ylaminocarbonyl]pyrrolidine hydrochloride → (2S,4S)-4-Mercapto-2-[(3R)-1-(N-4-nitrobenzyloxycarbonylacetimidoyl)pyrrolidin-3-ylaminocarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 362046Notes

Reaction equation

HRID 362046 reaction equation
Cl.COC1C=CC(C[S:9][C@@H:10]2[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)=[O:16])[C@H:12]([C:28]([NH:30][C@@H:31]3[CH2:35][CH2:34]N[CH2:32]3)=[O:29])[CH2:11]2)=CC=1.[N+:38]([C:41]1[CH:54]=[CH:53][C:44]([CH2:45][O:46][C:47]([NH:49][C:50](=[NH:52])[CH3:51])=[O:48])=[CH:43][CH:42]=1)([O-:40])=[O:39]>>[SH:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[C@H:12]([C:28]([NH:30][C@@H:31]2[CH2:35][CH2:34][N:52]([C:50](=[N:49][C:47]([O:46][CH2:45][C:44]3[CH:43]=[CH:42][C:41]([N+:38]([O-:40])=[O:39])=[CH:54][CH:53]=3)=[O:48])[CH3:51])[CH2:32]2)=[O:29])[CH2:11]1

Participants

3

Reactant 2

HCID 67586513(2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-[(3R)-pyrrolidin-3-ylaminocarbonyl]pyrrolidine hydrochlorideHCID 140352007HCID 140352007, compound

Product 1

HCID 88299617(2S,4S)-4-Mercapto-2-[(3R)-1-(N-4-nitrobenzyloxycarbonylacetimidoyl)pyrrolidin-3-ylaminocarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 53.1%

Procedure

Following a procedure similar to that described in Preparation 23(iii) and 23(iv), but using 0.76 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-[(3R)-pyrrolidin-3-ylaminocarbonyl]pyrrolidine hydrochloride and 0.33 g of N-(4-nitrobenzyloxycarbonyl)acetamidine, 0.45 g of the title compound was obtained as a powder.

Sources & evidence

ORD record
ord-03a41344533c475aaf24839ce4b041fa
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

Loading…