Pyridine → HCID 86756586, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (RS)-4-[2-formyl-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid (0.7 g), O-benzylhydroxylamine hydrochloride (0.48 g) and pyridine (1 mL) in ethanol (50 mL) is heated at 65° C. for 5 hours. The reaction mixture is evaporated. The residue is dissolved dichloromethane (80 mL), washed with 1 N hydrochloric acid, then with water, dried over magnesium sulphate and evaporated. The resulting oil is purified by flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95:5 v/v). Fractions homogeneous in the required product are combined, evaporated and the solid residue triturated with pentane to give (RS)-4-[2-(benzyloxyiminomethyl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid hydrate (0.2 g) as a cream coloured solid, m.p. 35-37° C. [Elemental analysis:- C,69.2; H,5.60; N,2.58; S,6.26%. Calculated for C25H23NO8.0.3H2O: - C,69.2; H,5.72; N,2.69; S,6.16%]

Provenance & Evidence