Trifluoromethanesulfonic acid → HCID 86752005, compound

HRID 362075Notes

Reaction equation

HRID 362075 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].COC1C=CC(C[S:16][C@@H:17]2[CH2:21][N:20]([CH3:22])[C@H:19]([C:23]([N:25]3[CH2:30][CH2:29][N:28]([N+:31]([O-:33])=[O:32])[CH2:27][CH:26]3[C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])=[O:24])[CH2:18]2)=CC=1>C1(OC)C=CC=CC=1>[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].[SH:16][C@@H:17]1[CH2:21][N:20]([CH3:22])[C@H:19]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([N+:31]([O-:33])=[O:32])[CH2:27][CH:26]2[C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])=[O:24])[CH2:18]1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 67585555HCID 67585555, compound

Product 1

HCID 86752005HCID 86752005, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

130 ml of trifluorocacetic acid and 4.6 ml of trifluoromethanesulfonic acid were added dropwise to a solution of 13.8 g of (2S,4S)-4-(4-methoxybenzylthio)-2-(4-nitrobenzyloxycarbonyl-1-piperazinylcarbonyl)-1-methylpyrrolidine [prepared as described in step (i) above] in 28.3 ml of anisole, and the resulting mixture was stirred for 30 minutes, whilst ice-cooling. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was washed with hexane and ether, in that order, by decantation to give 13.9 g of the title compound as a powder.

Workup

  1. temperaturecooling
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. washthe resulting residue was washed with hexane and ether, in that order, by decantation

Sources & evidence

ORD record
ord-7518d23a187143d982146382998f0f36
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

Loading…