Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetate: (49 mg, 0.09 mmol) in THF/CH3OH (1.0 mL/1.0 mL) was added 2N NaOH (0.44 mL, 0.9 mmol). The reaction mixture was heated at 50° C. for 2 h and the crude was purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the product. LCMS-ESI+: calc'd for C29H28ClN3O3S: 534.2 (M+H+); Found: 534.2 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.82 (d, J=1.6 Hz, 1H), 8.41 (d, J=2 Hz, 1H), 7.82 (s, 1H), 7.70-7.58 (m, 5H), 5.25 (s, 1H), 3.80 (s, 3H), 2.61 (s, 3H), 2.49 (s, 3H), 0.97 (s, 9H).

Provenance & Evidence