Trifluoroacetic acid → HCID 86752009, compound

HRID 727693Notes

Reaction equation

HRID 727693 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 67881956HCID 67881956, compound

Product 1

HCID 86752009HCID 86752009, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

2.56 g of (2S,4S)-2-[(3R)-3-dimethylamino-1-pyrrolidinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (1) above] were suspended in 5.1 ml of anisole, and 25.5 ml of trifluoroacetic acid and 0.83 ml of trifluoromethanesulfonic acid were added, whilst ice-cooling, to the resulting suspension. The mixture was then stirred at room temperature for 3 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, 1,2-dichloroethane was added to the residue, and excess acid was removed by azeotropic distillation. The residue was decanted using hexane and then triturated with diethyl ether, after which the mixture was decanted and dried by evaporation under reduced pressure to give 3.65 g of the title compound as a powdery product.

Workup

  1. temperaturecooling, to the resulting suspension
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure, 1,2-dichloroethane
  3. additionwas added to the residue, and excess acid
  4. customwas removed by azeotropic distillation
  5. customThe residue was decanted
  6. customtriturated with diethyl ether
  7. customafter which the mixture was decanted
  8. customdried by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f3a19a6caab346a6857b66300de9bdaa
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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