Sodium Carbonate → (S)-chloromethyl 2-((tert-butoxycarbonyl)amino)propanoate

Participants

Reaction Steps

To a vigorously stirred mixture of (S)-2-((tert-butoxycarbonyl)amino)propanoic acid (1 g, 5.29 mmol), tetrabutylammonium hydrogen sulfate (0.359 g, 1.057 mmol), and Na2CO3 (2.80 g, 26.4 mmol) in DCM 20 (mL) and water (20 mL) cooled in an ice/water bath was slowly added chloromethyl chlorosulfate (1.09 mL, 10.57 mmol) over a 4 min period. After stirring in ice/water bath for 30 min the cold bath was removed and the reaction allowed to stir at room temperature. After stirring 16 h at room temperature the reaction was diluted with water and extracted with DCM. The aqueous layer was back extracted with DCM and the combined organic layers were dried over MgSO4, filtered and concentrated to afford Preparation 5A (1.64 g).

Provenance & Evidence