Sodium Azide → HCID 86628918, compound

Participants

Reaction Steps

Following the general procedure for the preparation of azides of Description 16, [2,2-dimethyl-3-(phenylmethoxy)propanoyloxy]ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (46a) (0.47 g, 0.77 mmol, max.) dissolved in 4 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 90 mg (1.4 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 n-heptane (Hptn) (EtOAc/Hptn=1:4) as eluent to provide a mixture of 0.13 g (27% yield) of the title compound (46b). Rf=0.17 (EtOAc/Hept=1:4). MS (ESI) m/z 642.20 (M+Na)+.

Provenance & Evidence