Trifluoromethanesulfonate → (2S,4S)-4-Mercapto-2-[4-(N-4-nitrobenzyloxycarbonylformimidoyl)homopiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 727628Notes

Reaction equation

HRID 727628 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]([N:30]3[CH2:36][CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[O:29])[CH2:11]2)=CC=1.[N+:39]([C:42]1[CH:54]=[CH:53][C:45]([CH2:46][O:47][C:48]([NH:50][CH:51]=N)=[O:49])=[CH:44][CH:43]=1)([O-:41])=[O:40].FC(F)(F)S([O-])(=O)=O>>[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]([N:30]2[CH2:36][CH2:35][CH2:34][N:33]([CH:51]=[N:50][C:48]([O:47][CH2:46][C:45]3[CH:53]=[CH:54][C:42]([N+:39]([O-:41])=[O:40])=[CH:43][CH:44]=3)=[O:49])[CH2:32][CH2:31]2)=[O:29])[CH2:11]1

Participants

4

Reactant 3

HCID 2758875TrifluoromethanesulfonateHCID 22881639(2S,4S)-4-(4-methoxybenzylthio)-2-(1-homopiperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochlorideHCID 140386401(4-nitrophenyl)methyl N-methanimidoylcarbamate

Product 1

HCID 88300258(2S,4S)-4-Mercapto-2-[4-(N-4-nitrobenzyloxycarbonylformimidoyl)homopiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Procedure

Following a procedure similar to that described in Preparation 4, but using 2.10 g of (2S,4S)-4-(4-methoxybenzylthio)-2-(1-homopiperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride [prepared as described in Preparation 2(i)] and 0.93 g of N-(4-nitrobenzyloxycarbonyl)formamidine, 2.38 g of the trifluoromethanesulfonate of the title compound were obtained. The salt was treated by the same procedure as described in Preparation 4(ii), to give 1.90 g of the title compound.

Workup

  1. customthat described in Preparation 4

Sources & evidence

ORD record
ord-d1dee884d94d4f0bbb2b175d2528009b
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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