Sodium Bicarbonate → HCID 67526810, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-hydroxy-3-(4-hydroxymethylphenoxy)-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide (prepared in Example 70, 950 mg, 0.002636 mol) in dry CH2Cl2 (6.5 ml) was treated with Deoxo-Fluor® (875 mg, 0.003954 mol) in CH2Cl2 (3 ml) at −76° C. The solution was stirred at −10° C. for 3 hours. 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 heptane/ethyl acetate as a gradient eluent (9:1-5:5). Crystallization from dichloromethane/heptane gave the desired compound. 1H NMR (400 MHz, DMSO-d6): 1.44 (3H, s), 2.53 (3H, s), 4.00 (1H, d, 2Jgem=9.7 Hz), 4.24 (1H, d, 2Jgem=9.6 Hz), 5.30 (2H, d, 2JHF=48.6 Hz), 6.21 (1H, s, —OH), 6.95 (2H, d, 3J=8.4 Hz), 7.34 (2H, d, 3J=8.6 Hz), 7.84 (1H, dd, 3J=9.0 Hz, 4J=2.0 Hz), 7.93 (1H, broad s), 8.03 (1H, d, 3J=9.0 Hz), 10.14 (1H, s, —NHCO—).

Provenance & Evidence