Trifluoromethanesulfonic acid → HCID 86753694, compound

HRID 362054Notes

Reaction equation

HRID 362054 reaction equation
FC(F)(F)S(O)(=O)=O.COC1C=CC(C[S:16][C@@H:17]2[CH2:21][N:20]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])[C@H:19]([C:35]([N:37]3[CH2:42][CH2:41][CH:40]([N:43]4[CH:47]=[CH:46][N:45]=[CH:44]4)[CH2:39][CH2:38]3)=[O:36])[CH2:18]2)=CC=1.C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OCC)(=O)C>[SH:16][C@@H:17]1[CH2:21][N:20]([C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=2)=[O:23])[C@H:19]([C:35]([N:37]2[CH2:38][CH2:39][CH:40]([N:43]3[CH:47]=[CH:46][N:45]=[CH:44]3)[CH2:41][CH2:42]2)=[O:36])[CH2:18]1

Participants

7

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 67585037HCID 67585037, compound

Product 1

HCID 86753694HCID 86753694, compoundYield 100.7%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Procedure

350 μl of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 1.44 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[4-(imidazol-1-yl)piperidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (i) above] in a mixture of 1.5 ml of anisole and 7.5 ml of trifluoroacetic acid, and the resulting mixture was stirred at room temperature for 1 hour and then at 35° C. for a further 30 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was washed four times with diethyl ether to give a colorless powder. The whole of this powder was suspended in ethyl acetate and the suspension was made alkaline by the addition of an aqueous solution of sodium hydrogencarbonate. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, to give 1.15 g of the title compound, as a colorless powder.

Workup

  1. waitat 35° C. for a further 30 minutes
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. washthe residue was washed four times with diethyl ether
  4. customto give a colorless powder
  5. customThe ethyl acetate layer was separated
  6. washwashed with an aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-530e3c14657c4c47a069c5313ed084c7
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

Loading…