Trifluoroacetic acid → (2S)-2-Amino-N,3,3-trimethylbutanamide
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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
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° C. is added trifluoroacetic acid (320 mL). The resulting solution is allowed to warm to 25° 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
- concentrationThe reaction mixture is concentrated
- extractionextracted with 4:1 dichloromethane/isopropanol (1000 mL)
- washThe organic layer is washed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-21f2b2697b6c47159511c5da52318119
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06172064B2
Reaction notes
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