Trifluoroacetic acid → HCID 86747838, compound

HRID 1033673Notes

Reaction equation

HRID 1033673 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])[CH:11]([C:27](=[O:37])[NH:28][CH:29]3[CH:34]4[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]4)[CH2:30]3)[CH2:10]2)=CC=1.FC(F)(F)C(O)=O.[F:47][C:48]([F:54])([F:53])[S:49]([OH:52])(=[O:51])=[O:50]>C1(OC)C=CC=CC=1>[F:47][C:48]([F:54])([F:53])[S:49]([OH:52])(=[O:51])=[O:50].[F:47][C:48]([F:54])([F:53])[S:49]([OH:52])(=[O:51])=[O:50].[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])[CH:11]([C:27](=[O:37])[NH:28][CH:29]2[CH:34]3[CH2:33][CH2:32][N:31]([CH2:36][CH2:35]3)[CH2:30]2)[CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 15282191HCID 15282191, compound

Product 1

HCID 86747838HCID 86747838, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

770 mg of (4S)-4-(4-methoxybenzylthio)-2-[(3-quinuclidinyl)carbamoyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 6) were suspended in 1.5 ml of anisole, and the suspension was placed on an ice bath. Whilst the suspension was still on the ice bath, 6.5 ml of trifluoroacetic acid and 246 μl of trifluoromethanesulfonic acid were added to it, and the resulting mixture was stirred for 1.5 hours at room temperature. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was washed with hexane; the produce was then precipitated by the addition of diethyl ether, and the mixture was filtered, to give 813 mg of the title compound.

Workup

  1. customthe suspension was placed on an ice bath
  2. additionwere added to it
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. washthe resulting residue was washed with hexane
  5. customthe produce was then precipitated by the addition of diethyl ether
  6. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-719b85ca6c1f4e7b9d9e6482a74bc0b1
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

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