Hydrochloric Acid → HCID 58778867, compound

Participants

Reaction Steps

In methylene chloride (20 ml), EDC(HCl (691 mg, 3.6 mmol) was added at 0° C. to methyl 4-(1-(tert-butoxycarbonyl)-(2S)-pyrrolidinylmethoxy)cyclohexanecarboxylate (580 mg, 2.4 mmol), 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (678 mg, 2.4 mmol), HOBt (324 mg, 2.4 mmol) and triethylamine (1.0 ml, 7.2 mmol). The reaction mixture was stirred at room temperature for 16 hours. Ice water (10 ml) was added and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate, a 2M aqueous citric acid solution and a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (1:2, v/v) eluate fractions, the title compound (500 mg, 48%) was obtained as a colorless oil.

Provenance & Evidence