Trifluoroacetic acid → HCID 86753706, compound

HRID 362114Notes

Reaction equation

HRID 362114 reaction equation
COC1C=CC(C[S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27]([N:29]3[CH2:33][CH2:32][C@H:31]([N:34]4[CH:38]=[N:37][CH:36]=[N:35]4)[CH2:30]3)=[O:28])[CH2:10]2)=CC=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1.C(OCC)(=O)C>[SH:8][C@@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([C:27]([N:29]2[CH2:33][CH2:32][C@H:31]([N:34]3[CH:38]=[N:37][CH:36]=[N:35]3)[CH2:30]2)=[O:28])[CH2:10]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 67585187HCID 67585187, compound

Product 1

HCID 86753706HCID 86753706, compoundYield 115.6%

Reagents, catalysts & solvents 2

HCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Procedure

783 mg of (2S, 4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-(1-1,2,4-triazolyl)-1-pyrrolidinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (a) above] were suspended in 1.5 ml of anisole, and 7.5 ml of trifluoroacetic acid and 0.24 ml of trifluoromethanesulfonic acid were added to the resulting suspension, whilst ice-cooling, after which the mixture was stirred at room temperature for 1.5 hours. A cycle consisting of removing the solvent by evaporation under reduced pressure, washing the residue with hexane to remove anisole, adding diethyl ether to the mixture to solidify the product and milling the product, after which the mixture was decanted was repeated several times to obtain a powder. The whole of this powder was mixed with 40 ml of ethyl acetate and with an aqueous solution of sodium hydrogencarbonate, and then the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated by evaporation under reduced pressure, to give 713 mg of the title compound, as a powder.

Workup

  1. temperaturecooling
  2. customof removing the solvent
  3. customby evaporation under reduced pressure
  4. washwashing the residue with hexane
  5. customto remove anisole
  6. additionadding diethyl ether to the mixture
  7. customafter which the mixture was decanted
  8. customto obtain a powder
  9. customthe organic layer was separated
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fb36a938d98c4caea73a60c6f865845c
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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