HCID 54100298, compound → (R)-4,4,4-trifluoro-2-methyl-N-[(S)-1-phenylethyl]butyramide

HRID 327812Notes

Reaction equation

HRID 327812 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][CH:4]([CH3:16])[C:5]([NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:6]>O>[F:1][C:2]([F:17])([F:18])[CH2:3][C@@H:4]([CH3:16])[C:5]([NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:6]

Participants

3

Reactant 1

HCID 54100298HCID 54100298, compound

Product 1

HCID 10967206(R)-4,4,4-trifluoro-2-methyl-N-[(S)-1-phenylethyl]butyramideYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Impure 4,4,4-trifluoro-2-methyl-N-[(S)-1-phenylethyl]butyramide (94(R):6(S)) (5.0 g), prepared by a method similar to that described in step a) above, was dissolved in industrial methylated spirits (18.75 ml) by heating under reflux with stirring. Water (18.75 ml) was then added slowly, while continuing to heat the solution under reflux. The mixture was then heated under reflux for a further 45 minutes, and was then allowed to cool to room temperature, with continued stirring, overnight. The mixture was then filtered, and the crystalline product was washed with water (10 ml) and dried at 65° C. to give the title compound 4.45 g (89%). The product contained only 0.3% of the unwanted (S)-diastereomer.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. temperatureto heat the solution
  4. temperatureunder reflux
  5. temperatureThe mixture was then heated
  6. temperatureunder reflux for a further 45 minutes
  7. filtrationThe mixture was then filtered
  8. washthe crystalline product was washed with water (10 ml)
  9. customdried at 65° C.

Sources & evidence

ORD record
ord-c067e452242b46e68cdbcb0885d992ec
Source dataset
uspto-grants-1993_12
Patent number
US05274118

Reaction notes

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