Potassium tert-butoxide → HCID 68428251, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-tert-Butyl-phenyl)-4-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiazole-5-carboxylic acid ethy este (1.11 g, 2.0 mmol) was dissolved in 21 mL of anhydrous THF and cooled to −15° C. in a brine dry ice bath. A solution of 4.4 mL of 1.0 M potassium tert-butoxide in THF was added slowly to cold solution, and the reaction was stirred at −15° C. for 30 min. and then at room temperature for 2 h. The reaction was quenched with 4.4 mL of 1N HCl and 150 mL of saturated ammonium chloride aqueous solution, and extracted twice with 150 mL of chloroform. The organic fractions were washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-70% ethyl acetate in hexanes to produce 0.5 g of a yellow froth. MS: (+) m/z 508.9 (M+1).

Provenance & Evidence