Sodium Azide → HCID 86628915, compound

Participants

Reaction Steps

Following the general procedure for the preparation of azides of Description 16, (cyclohexylcarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (44a) (1.6 g, 3.0 mmol) dissolved in 15 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 0.65 g (10.0 mmol) of sodium azide (NaN3). After work-up, the crude material 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 1.1 g (65% yield) of the title compound (44b) as a colorless oil. Rf=0.30 (EtOAc/Hxn=1:4). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.04-1.06 (m, 6H), 1.19-1.30 (br. m, 3H), 1.40-1.49 (br. m, 2H), 1.51 (d, J=5.6 Hz, 3H), 1.62-1.66 (br. m, 1H), 1.70-1.78 (br. m, 2H), 1.85-1.94 (br. m, 2H), 2.01-2.08 (m, 2H), 2.24-2.37 (m, 1H), 3.09-3.15 (m, 2H), 3.43-3.47 (m, 2H), 3.81-3.83 (2s, 1H), 3.93 (d, J=8.8 Hz, 1H), 4.17-4.22 (m, 1H), 4.32-4.36 (2d, J=11.6, 11.2 Hz, 1H), 4.56-4.65 (2d, J=11.6, 11.6 Hz, 1H), 6.91-6.95 (m, 1H), 7.32-7.37 (m, 5H) ppm. MS (ESI) m/z 562.13 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence