1-Chloroethyl Cyclohexyl Carbonate → HCID 86628911, compound

Participants

Reaction Steps

Following the general procedure for the preparation of acyloxyalkyl/alkoxycarbonyloxyalkyl carboxylic esters from carboxylic acids of Description 22, (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoic acid (11) (0.4 g, 1.0 mmol) dissolved in 5 mL of anhydrous toluene was reacted with 0.67 g (4.0 mmol) of 1-chloroethyl cyclohexyloxyformate in the presence of 0.55 g (2.0 mmol) of silver carbonate (Ag2CO3). After work-up, the crude product was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:4) as eluent to provide 0.41 g (71% yield) of the title compound (43a). Rf=0.40 (EtOAc/Hxn=1:4). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.06-1.08 (m, 6H), 1.25-1.58 (br. m, 9H), 1.73-1.78 (br. m, 2H), 1.88-1.95 (br. m, 2H), 2.24-2.31 (m, 2H), 3.20-3.25 (m, 2H), 3.63-3.66 (m, 2H), 3.84-3.85 (2s, 1H), 3.94-3.97 (2d, J=9.2, 8.8 Hz, 1H), 4.19-4.23 (2d, J=9.2, 8.8 Hz, 1H), 4.33-4.38 (2d, J=11.2, 11.6 Hz, 1H), 4.55-4.70 (m, 2H), 6.81-6.87 (m, 1H), 7.31-7.37 (m, 5H) ppm. MS (ESI) m/z 571.05 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence