Sodium Hydroxide → 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-(((R)-5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid

Participants

Reaction Steps

To a solution of ethyl 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-(((R)-5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (1, 1.227 mmol) in Ethanol (12 mL) was added 1N NaOH (1.227 mL, 1.227 mmol) and the resulting mixture was stirred at room temp for 4 h. Mixture was then concentrated and the residue was diluted with water (10 mL) and extracted with ether (50 mL). The aqueous layer was then acidified with 1N HCl and extracted with ether (50 mL), washed with brine (10 mL), dried (Na2SO4), filtered and concentrated to afford 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-(((R)-5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid (920 mg, 1.169 mmol, 95% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.73-7.68 (m, 4H), 7.47-7.35 (m, 6H), 7.13 (s, 1H), 5.85 (br.s, 1H), 4.30-4.16 (m, 2H), 3.94-3.84 (m, 1H), 3.35 (q, J=6.3 Hz, 2H), 2.65 (s, 3H), 1.92 (d, J=10.7 Hz, 2H), 1.67-1.39 (m, 12H), 1.30 (s, 3H), 1.28-1.25 (m, 3H), 1.24 (s, 9H), 1.11-1.08 (m, 3H), 1.07 (s, 9H). LCMS (M+H)=787.4.

Provenance & Evidence