Trifluoroacetic acid → HCID 22881636, compound

HRID 727691Notes

Reaction equation

HRID 727691 reaction equation
[CH3:1][N:2]([CH3:38])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([C@@H:10]2[CH2:14][C@H:13]([S:15]CC3C=CC(OC)=CC=3)[CH2:12][N:11]2[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[O:26])=[O:9])[CH2:4]1.FC(F)(F)C(O)=O.[F:46][C:47]([F:53])([F:52])[S:48]([OH:51])(=[O:50])=[O:49]>C1(OC)C=CC=CC=1>[F:46][C:47]([F:53])([F:52])[S:48]([OH:51])(=[O:50])=[O:49].[CH3:1][N:2]([CH3:38])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([C@@H:10]2[CH2:14][C@H:13]([SH:15])[CH2:12][N:11]2[C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)=[O:26])=[O:9])[CH2:4]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 10840224HCID 10840224, compound

Product 1

HCID 22881636HCID 22881636, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

845 mg of (2S,4S)-2-[(3S)-3-dimethylamino-1-pyrrolidinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (1) above] were suspended in 1.7 ml of anisole, and 8.5 ml of trifluoroacetic acid and 0.28 ml of trifluoromethanesulfonic acid were added to the resulting suspension, whilst ice-cooling, after which the mixture was stirred at room temperature for 1 hour. The cycle comprising removing the solvent by evaporation under reduced pressure, washing the residue with hexane to remove anisole, adding diethyl ether to the mixture, cooling the mixture to -78° C. to solidify the product and milling the product, followed by decantation, was repeated several times to obtain 1.14 g of the title compound as a powder.

Workup

  1. temperaturecooling
  2. customThe cycle comprising 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. temperaturecooling the mixture to -78° C.

Sources & evidence

ORD record
ord-64173cbf90ca4148a6b6f31153e38a22
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

Loading…