Trifluoroacetic acid → HCID 86752014, compound

HRID 362116Notes

Reaction equation

HRID 362116 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[CH2:32][CH:31]([N:33]4[CH:37]=[N:36][CH:35]=[N:34]4)[CH2:30]3)=[O:28])[CH2:10]2)=CC=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>C1(OC)C=CC=CC=1>[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[CH2:30][CH:31]([N:33]3[CH:37]=[N:36][CH:35]=[N:34]3)[CH2:32]2)=[O:28])[CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 86752015HCID 86752015, compound

Product 1

HCID 86752014HCID 86752014, compoundYield 130%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
0 °C

Procedure

858 mg of (2S, 4S)-4-(4-methoxybenzylthio)-2-[3-(1-1,2,4-triazolyl)-1-azetidinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (a) above] were suspended in 1.7 ml of anisole, and 8.4 ml of trifluoroacetic acid and 0.27 ml of trifluoromethanesulfonic acid were added to the resulting suspension, whilst ice-cooling, after which the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 30 minutes. At the end of this time, the solvent was removed by evaporation under reduced pressure, and the residue was washed with hexane to remove anisole. The mixture was then mixed with diethyl ether to wash the mixture further. The resulting compound was mixed with 100 ml of ethyl acetate and with 30 ml of a saturated aqueous solution of sodium hydrogencarbonate, and the organic layer was separated. The organic layer was then dried over anhydrous magnesium sulfate, and the residue was filtered and concentrated by evaporation under reduced pressure, to give 873 mg of the title compound, as a white powder.

Workup

  1. temperaturecooling
  2. waitat room temperature for 30 minutes
  3. customAt the end of this time, the solvent was removed by evaporation under reduced pressure
  4. washthe residue was washed with hexane
  5. customto remove anisole
  6. additionThe mixture was then mixed with diethyl ether
  7. washto wash the mixture further
  8. additionThe resulting compound was mixed with 100 ml of ethyl acetate and with 30 ml of a saturated aqueous solution of sodium hydrogencarbonate
  9. customthe organic layer was separated
  10. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  11. filtrationthe residue was filtered
  12. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-bf85c725e0db4372bb7416a4e1255bbe
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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