Trifluoroacetic acid → (2S,4S)-4-Mercapto-1-methyl-2-[4-(4-nitrobenzyloxycarbonyl)-1-homopiperazinylcarbonyl]pyrrolidine trifluoromethanesulfonate
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]([CH3:29])[C@H:26]([C:30]([N:32]3[CH2:38][CH2:37][CH2:36][N:35]([C:39]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][CH:44]=4)=[O:40])[CH2:34][CH2:33]3)=[O:31])[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]([CH3:29])[C@H:26]([C:30]([N:32]2[CH2:38][CH2:37][CH2:36][N:35]([C:39]([O:41][CH2:42][C:43]3[CH:44]=[CH:45][C:46]([N+:49]([O-:51])=[O:50])=[CH:47][CH:48]=3)=[O:40])[CH2:34][CH2:33]2)=[O:31])[CH2:25]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
25 ml of trifluoroacetic acid and 0.83 ml of trifluoromethanesulfonic acid were added dropwise, whilst ice-cooling to a solution of 2.5 g of (2S,4S)-4-(4-methoxybenzylthio)-1-methyl-2-[4-(4-nitrobenzyloxycarbonyl)-1-homopiperazinylcarbonyl]-pyrrolidine [prepared as described in step (iii) above] in 5.2 ml of anisole, and the resulting mixture was stirred at the same temperature for 50 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was decanted, in turn, with hexane and with diethyl ether, to give 2.7 g of the title compound as an amorphous solid.
Workup
- concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
- customthe residue was decanted, in turn, with hexane and with diethyl ether
Sources & evidence
- ORD record
- ord-d4ac4e0c578143bea95b9e63849b11e7
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866564
Reaction notes
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