Sodium Hydroxide → (2S)-2-(tert-butoxy)-2-(7-(8-fluoro-5-methylchroman-6-yl)-2-((4-fluorobenzyl)carbamoyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid

Participants

Reaction Steps

A solution of (2S)-ethyl 2-(tert-butoxy)-2-(7-(8-fluoro-5-methylchroman-6-yl)-2-((4-fluorobenzyl)carbamoyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (12 mg, 0.020 mmol) and 1M NaOH (0.079 mL, 0.079 mmol) in MeOH (1 mL) was heated at 60° C. for 16 h. Then, the reaction mixture was cooled and purified by prep HPLC to afford (2S)-2-(tert-butoxy)-2-(7-(8-fluoro-5-methylchroman-6-yl)-2-((4-fluorobenzyl)carbamoyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid (8 mg, 0.013 mmol, 66.4% yield) as white solid. 1H NMR (500 MHz, CHLOROFORM-d) δ: 7.31 (dd, J=8.5, 5.5 Hz, 2H), 7.26 (t, J=6.4 Hz, 1H), 7.21 (s, 1H), 7.05-6.99 (m, 2H), 6.87 (d, J=10.7 Hz, 1H), 5.02 (s, 1H), 4.60 (d, J=6.4 Hz, 2H), 4.35-4.32 (m, 2H), 2.77 (s, 3H), 2.76-2.71 (m, 2H), 2.20-2.14 (m, 2H), 1.85 (s, 3H), 1.19 (s, 9H). LCMS (M+H)=579.4.

Provenance & Evidence