Dichloromethane → HCID 69669853, compound

Participants

Reaction Steps

To a stirring mixture of (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (2.4 g, 5.27 mmol), tetra(n-butyl)ammonium bisulfate (178.90 mg, 526.89 μmoles), and sodium bicarbonate (3.54 g, 42.15 mmol) in dichloromethane (13.2 mL) and water (13.2 mL) is added chloromethyl chlorosulfate (1.20 mL, 11.59 mmol). The mixture is stirred at ambient temperature for 18 hours. The reaction is poured over water and extracted with dichloromethane. The combined organics are dried over magnesium sulfate, filtered and concentrated to give a residue. The residue is purified by flash chromatography (20-35% ethyl acetate/hexane) to give the title compound (1.37 g, 2.48 mmol, 47% yield). MS (m/z): 574.0 (M+Na).

Provenance & Evidence