Methanol → Methyl 2-amino-4,4,4-trifluoro-3-(trifluoromethyl)butanoate

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Reaction Conditions

Reaction Steps

To a solution of 4,4,4,4′,4′,4′-hexafluoro-dl-valine (2.5 g, 11.11 mmol) in CH2Cl2-MeOH (4:1, 25 mL) at 0° C. was added TMS-diazomethane (2.0 M in hexane, 45 mmol, 23 mL) dropwise. The resulting neon greenish solution was stirred for 19 hours at 25° C. After this time period, the reaction was complete by TLC (10% MeOH in chloroform). After concentration, the resulting residue of methyl 4,4,4,4′,4′,4′-hexafluoro-dl-valinate (2.35 g) was used directly in the next step without further purification. Mass Spectrum (−ESI): 238 [M−H]−.

Provenance & Evidence