Lithium hydroxide, monohydrate → HCID 18957366, compound

Participants

Reaction Steps

A mixture of methyl [3-[[(4,5-diphenyl-2-oxazolyl) methyl](ethoxycarbonyl)amino]phenoxy]acetate (0.90 g, 1.9 mmol), LiOH.H2O (82 mg, 2 mmol) and 95% EtOH (25 mL) was stirred at room temperature for about 25 hours. The EtOH was evaporated, the residue diluted with H2O and acidified with 2N HCl solution. Extraction with CH2Cl2 afforded an oil which was chromatographed first on a column of silica gel using CH2Cl2 /MeOH (9:1) as eluent and subsequently on a column of silica gel using hexanes/EtOAc/AcOH (12:7:1) as eluent to give [3-[[(4,5-diphenyl-2-oxazolyl) methyl](ethoxycarbonyl)amino]phenoxy]acetic acid (0.70 g, 80%). IR (film) 3000, 1710 cm-1 ; 1H NMR (CDCl3) δ1.22 (3H, t, J=8 Hz, OCH2CH3), 4.21 (2H, q, J=8 Hz, OCH2CH 3), 4.55 (2H, s, OCH2CO2CH3), 5.03 (2H, s, CH2 -oxazole), 6.79 (1H, dd, J=9 Hz, J'=2 Hz, aromatic H), 7.00 (2H, m, aromatic H), 7.20 to 7.40 (7H, m, aromatic H), 7.50 to 7.70 (4H, m, aromatic H), 10.49 (1H, bs, CO2H); MS m/z 473 (MH+).

Provenance & Evidence