Thionyl Chloride → HCID 71008696, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (1S,2S)-rel-2-[(R)-2,2-difluoro-3-hydroxy-1-methyl-1-((R)-2-methyl-propane-2-sulfinylamino)-propyl]-cyclopropanecarboxylic acid tert-butyl ester (1.16 g, 3.14 mmol) in ethanol (22.5 ml) was treated dropwise at 0° C. with thionyl chloride (1.89 g, 1.15 ml, 15.7 mmol). The yellow mixture was then stirred at 85° C. for 2 hours. For the workup, the solvent was evaporated at reduced pressure, then water and diethyl ether were added. The aqueous layer was treated with carbonate, thereafter extracted three times with dichloromethane. The combined organic layers were dried over sodium sulphate and evaporated. The light yellow oil (708 mg) was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 0:100 as the eluent. The (1S,2S)-rel-2-((R)-1-amino-2,2-difluoro-3-hydroxy-1-methyl-propyl)-cyclopropane-carboxylic acid ethyl ester (566 mg, 76% yield) was obtained as a light yellow oil. MS (ISP): m/z=238.2 [M+H]+.

Provenance & Evidence