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

HRID 727624Notes

Reaction equation

HRID 727624 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].COC1C=CC(C[S:23][C@@H:24]2[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[C@H:26]([C:42]([N:44]3[CH2:50][CH2:49][CH2:48][N:47]([C:51](=[N:53][C:54]([O:56][CH2:57][C:58]4[CH:63]=[CH:62][C:61]([N+:64]([O-:66])=[O:65])=[CH:60][CH:59]=4)=[O:55])[CH3:52])[CH2:46][CH2:45]3)=[O:43])[CH2:25]2)=CC=1>C1(OC)C=CC=CC=1>[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[SH:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:30])[C@H:26]([C:42]([N:44]2[CH2:50][CH2:49][CH2:48][N:47]([C:51](=[N:53][C:54]([O:56][CH2:57][C:58]3[CH:59]=[CH:60][C:61]([N+:64]([O-:66])=[O:65])=[CH:62][CH:63]=3)=[O:55])[CH3:52])[CH2:46][CH2:45]2)=[O:43])[CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 88299641(2S,4S)-4-(4-Methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)homopiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 88299044(2S,4S)-4-Mercapto-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)homopiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine Trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

2.1 ml of trifluoroacetic acid and 67 μl of trifluoromethanesulfonic acid were added to a solution of 285 mg of (2S,4S)-4-(4-methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)homopiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (ii) above] in 414 μl of anisole, and the resulting mixture was stirred for 1 hour, whilst ice-cooling. At the end of this time, the reaction mixture was worked up by the same procedure as described in Preparation 1(iv), to give 296 mg of the title compound, as a powder.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-c4a4e21935c84276873f37659883b2cf
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

Loading…