Ethyl trifluoroacetate → HCID 86622344, compound

HRID 501720Notes

Reaction equation

HRID 501720 reaction equation
[NH2:1][C@H:2]([CH2:5][CH:6]([CH3:8])[CH3:7])[CH2:3][OH:4].[F:9][C:10]([F:17])([F:16])[C:11](OCC)=[O:12]>O>[F:9][C:10]([F:17])([F:16])[C:11]([NH:1][C@H:2]([CH2:5][CH:6]([CH3:8])[CH3:7])[CH2:3][OH:4])=[O:12]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 2724002D(-)-Leucinol

Product 1

HCID 86622344HCID 86622344, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step AK (1): (R)-2-amino-4-methylpentan-1-ol (1.0 g, 8.53 mmol) was dissolved in ethyl trifluoroacetate (2.5 mL). The reaction mixture was stirred overnight at rt. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with water and brine. The organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography to give (R)-2,2,2-trifluoro-N-(1-hydroxy-4-methylpentan-2-yl)acetamide (1.48 g, 81%) as a colorless oil. LC-MS (M+H)+=214.81.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialThe organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d801b339319c4b5e9cebfdff856c084d
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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