2,2,4-Trimethylpentane → HCID 9967975, compound

Participants

Reaction Steps

To a stirred solution of [4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]acetic acid (Step 1) (0.85 g, 2.37 mmol) in THF (25 mL) was added borane dimethylsulfide (0.47 mL of 10.0M solution, 4.74 mmol). After stirring at room temperature for 2 days, the reaction was quenched with aqueous KHSO4 (0.25M) and extracted with ethyl acetate. The combined ethyl acetate phases were washed with saturated NaHCO3 solution, brine, dried over MgSO4, filtered and concentrated in vacuo yielding a pale yellow solid. The crude product was dissolved in hot dichloromethane and isooctane was added to induce crystallization. Vacuum filtration of the resulting suspension yielded 4-[5-(2-hydroxyethyl)-3-phenylisoxazol-4-yl]benzenesulfonamide (0.276 g, 34%) as a pale yellow solid: mp 186°-190° C. 1H NMR (DMSO d6 /300 MHz) 7.81 (d, 2H, J=8.0 Hz), 7.48-7.28 (m, 9H), 4.95 (t, 1H, J=5.0 Hz), 3.70 (q, 2H, J=5.6 Hz), 2.92 (t, 2H, J=6.2 Hz). FABLRMS m/z 345 (M+H). FABHRMS m/z 345.0923 (M+H, C17H17N2O4S requires 345.0909). Anal. Calc'd for C17H17N2O4S.1.66 wt % H2O: C. 58.30; H, 4.79; N, 8.00. Found: C, 58.37; H, 4.89; N, 7.60.

Provenance & Evidence