Hydrochloric Acid → HCID 14774463, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-2-(tert-butoxycarbonylamino)-3-methylbutanoic acid (2.50 g, 11.5 mmol), HOBT-H2O (1.76 g, 11.5 mmol) and DIEA (6.01 mL, 34.5 mmol) in THF (50 mL) was cooled to 0° C. HBTU (3.23 g, 13.8 mmol) was added and the mixture stirred at 0° C. for 30 minutes prior to addition of 4-methoxy-benzylamine (2.25 mL, 17.3 mmol). The reaction mixture was allowed to warm slowly to ambient temperature while stirring over 48 hours. The reaction mixture was poured into 10% HCl and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification of the crude material by column chromatography, eluting with 1.5-3% MeOH/dichloromethane afforded (S)-tert-butyl 1-(4-methoxybenzylamino)-3-methyl-1-oxobutan-2-ylcarbamate as a light yellow solid, 2.70 g (70%).

Provenance & Evidence