Trifluoroacetic acid → (2S)-2-Amino-N,3,3-trimethylbutanamide

HRID 887946Notes

Reaction equation

HRID 887946 reaction equation
[CH3:1][NH:2][C:3](=[O:17])[C@@H:4]([NH:9]C(OC(C)(C)C)=O)[C:5]([CH3:8])([CH3:7])[CH3:6].FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C:3](=[O:17])[C@@H:4]([NH2:9])[C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10657950HCID 10657950, compound

Product 1

HCID 445856(2S)-2-Amino-N,3,3-trimethylbutanamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid methylamide (126 g, 519 mmol) in dichloromethane (320 mL) cooled at 0.degree. C. is added trifluoroacetic acid (320 mL). The resulting solution is allowed to warm to 25.degree. C. and is stirred for 18 h. The reaction mixture is concentrated, brought to pH=10 with 2 M sodium hydroxide, and extracted with 4:1 dichloromethane/isopropanol (1000 mL). The organic layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (2S)-2-Amino-3,3-dimethylbutanoic acid methylamide (40.5 g, 79% yield) as a white solid.

Workup

  1. temperatureto warm to 25.degree
  2. concentrationThe reaction mixture is concentrated
  3. extractionextracted with 4:1 dichloromethane/isopropanol (1000 mL)
  4. washThe organic layer is washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27a472827a334f668fd1562d2901e710
Source dataset
uspto-grants-2012_08
Patent number
US08247451B2

Reaction notes

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