Boc-L-3-Bromophenylalanine → 468740-94-5

Participants

Reaction Steps

To a solution of (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (Chem-Impex) (15 g, 44 mmol) in tetrahydrofuran (31 mL, 380 mmol) with stirring, 1.0 M borane-THF complex in THF (130 mL) was added dropwise to keep temperature at 0° C. (about 15 min). After addition the reaction mixture was stirred at room temperature for 1 h, cooled with an ice-bath, quenched with AcOH:MeOH (1:5, 70 mL), and partitioned between saturated aqueous NaHCO3 solution and DCM, dried over sodium sulfate and evaporated under reduced pressure to give 13.2 g (92% yield) of the crude desired product, which was used in the next reaction with no further purification. LC-MS found: 330.1 (M+H)+.

Provenance & Evidence