Dimethylformamide → HCID 86629054, compound

Participants

Reaction Steps

Following the general procedure for the preparation of carboxylic esters from carboxylic acids of Description 15, (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-acetyloxy-3,3-dimethylbutanoic acid (16) (0.31 g, 0.94 mmol) dissolved in 10 mL of anhydrous dichloromethane (DCM) was reacted with 0.56 mL (1.1 mmol) of oxalyl chloride (2.0 M in DCM) in the presence of a catalytic amount of N,N-dimethylformamide (DMF). After completion of the reaction, a solution of 0.28 mL of 3-pyridylmethanol (0.26 g, 2.3 mmol) in dichloromethane was added to the acid chloride. After work-up, the crude material was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and hexane (Hxn) as eluent (EtOAc/Hxn=2:1) to provide 0.22 g (54% yield) of the title compound (38a) as a colorless oil. Rf=0.55 (EtOAc). 1H NMR (400 MHz, CDCl3):): δ=1.03 (s, 3H), 1.05 (s, 3H), 2.10 (s, 3H), 2.22-2.30 (m, 2H), 3.24-3.28 (m, 2H), 3.62-3.66 (m, 2H), 3.92 (d, J=9.2 Hz, 1H), 4.12 (d, J=9.6 Hz, 1H), 4.77 (s, 1H), 5.15-5.22 (m, 2H), 7.30-7.34 (m, 1H), 7.70-7.73 (m, 1H), 8.54-8.59 (m, 2H) ppm. MS (ESI) m/z 422.00 (M+H)+. The analytical data was consistent with proposed structure.

Provenance & Evidence