Sodium Carbonate → (2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid

Participants

Reaction Steps

To a solution of (S)-2-aminobutanoic acid (11.2 g, 109 mmol) in THF (200 mL) and a 2 M aqueous sodium carbonate solution (65.2 ml, 130 mmol) was added dropwise at 0° C. benzyl carbonochloridate (17.06 mL, 119 mmol). After stirring at room temperature for 16 hours, the reaction mixture was extracted with H2O/TBME, the aqueous layer was acidified with HCl (2M in H2O) until pH=2 and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated to give the title compound (22.8 g, 77%) as a colorless oil. The product was used in the next step without further purification. LC-MS: [M−H] 236.2; Rt 0.76 min; (LCMS method 1).

Provenance & Evidence