Trifluoroacetic acid → HCID 22880269, compound

Participants

Reaction Steps

To an ice-cold solution of (S)-tert-butyl 1-(benzyl(methyl)amino)-1-oxopropan-2-ylcarbamate (26.3 g, 0.090 mol) in CH2Cl2 (100 mL) was added TFA(100 mL) drop wise. The reaction mixture was warmed to ambient temperature. After 18.5 h, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between CH2Cl2 (250 mL) and saturated NaHCO3 (250 mL). The aqueous layer was separated and basified to pH=9-10 with 1 N NaOH and extracted again with CH2Cl2 (100 mL). The combined organic layers were washed with saturated NaHCO3 (100 mL), H2O (100 mL), brine (100 mL), dried (Na2SO4) and concentrated under reduced pressure to give (S)-2-amino-N-benzyl-N-methylpropanamide (14.7 g, 85%) as an amber oil. 1H NMR consistent.

Provenance & Evidence