Triethylamine → HCID 67015830, compound

Participants

Reaction Steps

To a solution of N-(tert-butoxycarbonyl)-D,L-alanine (3.40 g, 17.9 mmol) and triethylamine (2.50 mL, 17.9 mmol) in THF (20 mL) was added 2-methylpropyl chlorocarbonate (2.33 mL, 17.9 mmol) under ice-cooling, and the mixture was stirred for 1 hr. To this solution was added dropwise a solution of methyl 3-amino-4-hydroxybenzoate (3.00 g, 17.9 mmol) in THF (10 mL) under a nitrogen atmosphere, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 0.5N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was triturated with hexane-chloroform (1:1) to give the title compound (2.57 g, yield 42%).

Provenance & Evidence