Lithium Hydroxide → HCID 71209270, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-methyl 2-(tert-butoxy)-2-(1-(3,4-difluorobenzyl)-4-(2,3-dihydrobenzofuran-5-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (126 mg, 0.242 mmol) in MeOH/THF/water=2/2/1 (10 mL) was treated with LiOH (110 mg, 4.59 mmol) and the mixture was heated at 70° C. until the reaction was judged complete. The mixture was concentrated, water was added and then adjusted to pH 2 with 1N HCl. The mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford (S)-2-(tert-butoxy)-2-(1-(3,4-difluorobenzyl)-4-(2,3-dihydrobenzofuran-5-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid (105 mg, 0.207 mmol, 86% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.62-7.47 (m, 1 H), 7.39-7.27 (m, 1 H), 7.16-7.05 (m, 2 H), 7.05-6.96 (m, 2 H), 6.92 (dd, J=4.7, 8.2 Hz, 1 H), 6.30-6.16 (m, 1 H), 5.64-5.54 (m, 1 H), 5.51-5.43 (m, 1 H), 5.43-5.33 (m, 1 H), 4.67 (td, J=4.2, 8.7 Hz, 2 H), 3.41-3.20 (m, 2 H), 2.70 (s, 3H), 0.99-0.89 (s, 9 H); LC/MS ES+=507.35 (M+1).

Provenance & Evidence