Hydrochloric Acid → 2-Amino-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester hydrochloride

HRID 905878Notes

Reaction equation

HRID 905878 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[N:12]O)[C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])[CH3:2].[ClH:15].[H][H]>C(O)C.[Pd]>[ClH:15].[CH2:1]([O:3][C:4](=[O:14])[CH:5]([NH2:12])[C:6](=[O:11])[C:7]([F:8])([F:9])[F:10])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178472917HCID 178472917, compound

Product 1

HCID 866376902-Amino-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester hydrochlorideYield 61.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of 4,4,4-trifluoro-2-hydroxyimino-3-oxo-butyric acid ethyl ester (55 g, 0.258 mol) in ethanol (140 ml) was added with palladium on activated carbon and 4N hydrochloric acid (90 ml) accordingly. The reaction mixture was stirred in a Parr shaker under 0.3 MPa of hydrogen at room temperature for 2.5 hours. The reaction mixture was filtered, the filtrate was concentrated to give 2-amino-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester hydrochloride (37.56 g, 61.8%) as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e4c32f2c8bed4ee68812b8e81314fc53
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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