benzyl (2S)-2-(4,4,4-trifluorobutanoylamino)propanoate → (2S)-2-(4,4,4-Trifluorobutanoylamino)propanoic acid

HRID 1045782Notes

Reaction equation

HRID 1045782 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][CH2:4][C:5]([NH:7][C@@H:8]([CH3:19])[C:9]([O:11]CC1C=CC=CC=1)=[O:10])=[O:6]>CO.[Pd]>[F:1][C:2]([F:20])([F:21])[CH2:3][CH2:4][C:5]([NH:7][C@@H:8]([CH3:19])[C:9]([OH:11])=[O:10])=[O:6]

Participants

4

Reactant 1

HCID 71244635benzyl (2S)-2-(4,4,4-trifluorobutanoylamino)propanoate

Product 1

HCID 79014130(2S)-2-(4,4,4-Trifluorobutanoylamino)propanoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add palladium/carbon (5%, 1.76 g, 0.8 mmol) in one portion to a solution of benzyl (2S)-2-(4,4,4-trifluorobutanoylamino)propanoate (8.80 g, 29 mmol) in methanol (88 mL) at ambient temperature. Degas the mixture (vacuum/nitrogen), fill with hydrogen (one atmosphere) and stir under hydrogen (29 mmol) for 5 hours. Filter through Celite®, rinse filter cake with methanol and concentrate the filtrate to obtain the title compound as a white solid (6.11 g, 28.7 mmol, 99%). MS (m/z): 214 (M+1); [α]Na25=−24.7° (c=5.0, methanol).

Workup

  1. customDegas the mixture (vacuum/nitrogen)
  2. filtrationFilter through Celite®
  3. washrinse
  4. filtrationfilter cake with methanol
  5. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-5be8a4c696df44c79951482cda20ab1c
Source dataset
uspto-grants-2013_10
Patent number
US08569286B2

Reaction notes

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