Ethyl bromoacetate → [Tert-butoxycarbonyl-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-ethyl]-amino]-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 10-7 (2.0 g, 7.8 mmol) and N,N-diisopropylethylamine (6.8 mL) in acetonitrile (50 mL) at 0° C. was added ethyl bromoacetate (0.975 mL, 8.6 mmol). The mixture was stirred at 50° C. for 15 h, then cooled to 25° C. and BOC2O (1.7 g, 7.8 mmol) was added. After 1 h, the mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 50-60% EtOAc/hexanes) gave 10-8 as a colorless oil.

Provenance & Evidence