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

HRID 727648Notes

Reaction equation

HRID 727648 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][NH:33][CH2:32]3)=[O:29])[CH2:11]2)=CC=1.[N+:38]([C:41]1[CH:53]=[CH:52][C:44]([CH2:45][O:46][C:47]([NH:49][CH:50]=N)=[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:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@H:12]([C:28]([NH:30][C@@H:31]2[CH2:35][CH2:34][N:33]([CH:50]=[N:49][C:47]([O:46][CH2:45][C:44]3[CH:52]=[CH:53][C:41]([N+:38]([O-:40])=[O:39])=[CH:42][CH:43]=3)=[O:48])[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 140386401(4-nitrophenyl)methyl N-methanimidoylcarbamate

Product 1

HCID 88299414(2S,4S)-4-Mercapto-2-[(3R)-1-(N-4-nitrobenzyloxycarbonylformimidoyl)pyrrolidin-3-ylaminocarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 52.9%

Procedure

Following a procedure similar to that described in Preparations 23(iii) and 23(iv), but using 1.38 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-[(3R)-pyrrolidin-3-ylaminocarbonyl]pyrrolidine hydrochloride and 564 mg of N-(4-nitrobenzyloxycarbonyl)formamidine, 795 mg of the title compound were obtained as a powder.

Sources & evidence

ORD record
ord-152f33b398444683bc44fbd4598afaf4
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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