Trifluoroacetic acid → HCID 178481176, compound

HRID 727727Notes

Reaction equation

HRID 727727 reaction equation
COC1C=CC(C[S:8][C@@H:9]2[CH2:13][N:12]([CH3:14])[C@H:11]([C:15]([N:17]3[CH2:20][CH:19]([NH:21][C:22](=[NH:37])[CH2:23][C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=4)=[O:25])[CH2:18]3)=[O:16])[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][CH:9]1[CH2:13][N:12]([CH3:14])[CH:11]([C:15]([N:17]2[CH2:20][CH:19]([NH:21][C:22](=[NH:37])[CH2:23][C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=3)=[O:25])[CH2:18]2)=[O:16])[CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 178491729HCID 178491729, compound

Product 1

HCID 178481176HCID 178481176, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

610 mg of (2S,4S)-4-(4-methoxybenzylthio)-1-methyl-2-[3-(N-4-nitrobenzyloxycarbonylacetimidoylamino)azetidin-1-ylcarbonyl]pyrrolidine [prepared as described in step (a) above] were dissolved in 1.19 ml of anisole, and 4.23 ml of trifluoroacetic acid and 193 μl of trifluoromethanesulfonic acid were added to the resulting solution, whilst ice-cooling. The mixture was then stirred for 1 hour under the same conditions and then at room temperature for a further 1 hour. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was washed with hexane and with diethyl ether and dried by evaporation under reduced pressure, to convert it to the trifluoromethanesulfonate in the form of a powder. Ethyl acetate was added to the whole of this compound, followed by sufficient of a saturated aqueous solution of sodium hydrogencarbonate to make it alkaline. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure, to give 448 mg of the title compound as a powder.

Workup

  1. temperaturecooling
  2. waitat room temperature for a further 1 hour
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. washthe resulting residue was washed with hexane and with diethyl ether
  5. customdried by evaporation under reduced pressure
  6. additionEthyl acetate was added to the whole of this compound
  7. customThe ethyl acetate layer was separated
  8. washwashed with an aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-38ee6db2ce4141648a112a64318caff7
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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