Sodium Bicarbonate → HCID 67526944, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-hydroxy-3-[4-(2-hydroxyethylphenoxy]-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide (prepared in Example 20, 300 mg, 0.0008012 mol) in dry CH2Cl2 (3 ml) was treated with Deoxo-Fluor® (195 mg, 0.0008813 mol) in dry CH2Cl2 (1 ml) at −15 to −10° C. The solution was stirred for 2 h at 0° C. and then for 3 days at room temperature. The saturated NaHCO3 solution was added and the mixture was extracted with dichloromethane. The combined extracts were washed with water, dried over Na2SO4, filtered, and evaporated in vacuo. The crude product was purified by flash chromatography using dichloromethane as an eluent. Crystallization from toluene afforded the desired compound as pure crystals: m.p. 102-105° C. 1H NMR (400 MHz, DMSO-d6): 1.43 (3H, s), 2.53 (3H, s), 2.88 (2H, dt, 3JHF=24.4 Hz, 3J=6.4 Hz), 3.95 (1H, d, 2Jgem=9.8 Hz), 4.18 (1H, d, 2Jgem=9.5 Hz), 4.56 (2H, dt, 2JHF=47.4 Hz, 3J=6.4 Hz), 6.18 (1H, broad s, —OH), 6.85 (2H, d, 3J=8.5 Hz), 7.15 (2H, d, 3J=8.4 Hz), 7.88 (1H, d, 3J=9.0 Hz), 7.93 (1H, s), 8.03 (1H, d, 3J=9.0 Hz), 10.13 (1H, broad s, —NHCO—).

Provenance & Evidence