Dimethylformamide → HCID 53678371, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-(5-(1,2-dihydroxy-ethyl)-pyridin-2-yl)-acetamide (0.294, 1.5 mmol) in anhydrous DMF (3 ml) was treated with triethylamine (0.63 g, 4.5 mmol) and cooled to −40° C. A solution of 4-nitrobenzenesulfonyl chloride (0.332 g, 1.5 mmol) in ethyl acetate (3 ml) was added dropwise. After 45 minutes at −45° C., the mixture was stirred for one hour at 20° C. The mixture was then diluted with ethyl acetate and washed sequentially with water, twice with pH 6.6 buffer (0.1 M phosphate), water and brine. The ethyl acetate layer was dried over sodium sulfate, filtered and evaporated. The residue was triturated with 1,2-dichloroethane to give 0.381 g (67%) of the title product as colorless crystals. mp 116-120° C. with decomposition. 1H NMR (dmso-d6): δ=8.36 (d, 2 H); 8.16 (d, 1 H); 8.04 (d, 2 H); 7.91 (d, 1 H); 7.62 (d of d, 1 H); 5.89 (d, 1 H); 4.81 (d of d, 1 H); 4.24 (d, 2 H); 2.06 (s, 3 H). MS (Cl): m/z=179 (M+H+-O2NC6H4SO3H).

Provenance & Evidence