Hydrochloric Acid → HCID 68705812, compound

Participants

Reaction Steps

To a stirring solution of methyl 5-(5-{(1R)-1-[(tert-butoxycarbonyl)amino]-1-methyl-2-phenylethyl}-1,3,4-oxadiazol-2-yl)-2′-cyanobiphenyl-3-carboxylate from Step A (780 mg, 1.45 mmole) in methanol (20 mL) at rt was added 0.43 mL of 5 N NaOH aq. The reaction was allowed to stir at rt overnight. The solution was poured into water (100 mL) and acidified by adding 1N HCl (10 mL). The resulting mixture was extracted with ethyl acetate (2×100 mL). The combined organics were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure to give 5-(5-{1-[(tert-butoxycarbonyl)amino]-1-methyl-2-phenylethyl}-1,3,4-oxadiazol-2-yl)-2′-cyanobiphenyl-3-carboxylic acid (Intermediate XVII). 1H NMR (400 MHz, CDCl3) δ 8.77 (br s, 1H), 8.47 (m, 2H), 7.84 (d, J=7.7 Hz, 1H), 7.72 (t, J=7.7 Hz, 1H), 7.65-7.55 (m, 2H), 7.33-7.25 (m, 3H), 7.13-7.05 (2H, m) 5.25 (br s, 1H), 3.61 (d, J=13.5 Hz, 1H), 3.46 (d, J=13.5 Hz, 1H), 1.76 (s, 3H), 1.42 (s, 9H). LCMS [(M)+H]+=525

Provenance & Evidence