Sodium Azide → HCID 86629043, compound

Participants

Reaction Steps

Following the general procedure for the preparation of azides of Description 16, phenylmethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoate (31a) (0.44 g, 0.9 mmol) dissolved in 5 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 81 mg (1.1 mmol) of sodium azide (NaN3). After work-up, the crude title compound (31b) was purified by silica gel column chromatography and used in the next step. Rf=0.59 (EtOAc/Hxn=1:2). 1H NMR (400 MHz, CDCl3): δ=1.02 (s, 6H), 1.98-2.10 (m, 2H), 3.07-3.13 (m, 2H), 3.63-3.65 (m, 2H), 3.81 (s, 3H), 3.85 (s, 1H), 3.94 (d, J=9.2 Hz, 1H), 4.18 (d, J=9.2 Hz, 1H), 4.27 (d, J=11.2 Hz, 1H), 4.53 (d, J=10.8 Hz, 1H), 5.20 (s, 2H), 6.85 (d, J=8.4 Hz, 2H), 7.20 (d, J=8.8 Hz, 2H), 7.37-7.39 (m, 5H) ppm. MS (ESI) m/z 528.15 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence