Sodium Carbonate → HCID 90079938, compound

Participants

Reaction Steps

To a stirred solution of 1-((tert-butoxycarbonyl)amino)cyclopropane-carboxylic acid (0.55 g, 2.73 mmol), sodium carbonate (1.449 g, 13.67 mmol) and tetrabutylammonium hydrogen sulfate (0.186 g, 0.547 mmol) in a mixture of DCM (10 mL) and water (5 mL) at 0° C., was added chloromethyl chlorosulfate (0.902 g, 5.47 mmol). The reaction mixture was allowed to warm to room temperature overnight. The mixture was diluted with DCM and water and the organic layer was separated, washed with a brine solution and dried over Na2SO4. The mixture was filtered and concentrated in vacuo and the residue obtained was purified by a flash chromatography (SiO2, 0-10% EtOAc in hexane) to afford Preparation 53A (0.5 g, 73.3%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 1.24-1.26 (m, 2H), 1.46 (s, 9H), 1.60-1.61 (m, 2H), 5.13 (s, 1H), 5.71 (s, 2H).

Provenance & Evidence