Trifluoromethanesulfonic acid → HCID 86751998, compound

HRID 362042Notes

Reaction equation

HRID 362042 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[CH2:41][CH2:40][C@H:39]([N:42]4[CH:46]=[CH:45][N:44]=[CH:43]4)[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[CH2:41][CH2:40][C@H:39]([N:42]3[CH:46]=[CH:45][N:44]=[CH:43]3)[CH2:38]2)=[O:36])[CH2:18]1

Participants

7

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 67586157HCID 67586157, compound

Product 1

HCID 86751998HCID 86751998, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Procedure

585 μl of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 2.5 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-(imidazol-1-yl)pyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (i) above] in a mixture of 5 ml of anisole and 15 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 mixture was concentrated by evaporation under reduced pressure, and the resulting residue was washed four times with diethyl ether, to give a colorless powder. 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 and washed with an aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.9 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 mixture was concentrated by evaporation under reduced pressure
  3. washthe resulting 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 materialafter which it was dried over anhydrous sodium sulfate
  8. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-344a336da7b343a5bbd6d4b8ba356ebe
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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