Lithium Hydroxide → HCID 58533722, compound

Participants

Reaction Steps

To a solution of ester 1.2a (800 mg, 3.29 mmol) in THF (16 ml) and MeOH (4 mL) was added a solution of LiOH (316 mg, 13.2 mmol) in water (4 mL) and stirred at room temperature for 4 h. The reaction was quenched upon addition of 1 N HCl (12 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were dried over MgSO4 and concentrated under vacuum. The residue was dissolved in DMF (24 mL) and DIPEA (1.22 mL, 6.80 mmol) and HATU (1.29 g, 3.40) added sequentially. The solution was placed into multiple vials and reacted with 3,3-dimethylbutylamine (0.18 mmol) and allowed to stir at rt for 20 h. The reaction was diluted with water (5 mL) and extracted with EtOAc (2×3 mL). The combined organic extracts were dried, concentrated and purified by mass-directed prep reverse-phase HPLC: 1H-NMR (400 MHz, CDCl3) δ 8.99 (s, 1H), 8.20 (d, J=8.0 Hz, 1H), 8.04 (s, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.36-7.26 (m, 2H), 7.06-6.97 (m, 3H), 6.24 (s, 1H), 5.30 (s, 2H), 3.58-3.50 (m, 2H), 1.81-1.75 (m, 1H), 1.59-1.49 (m, 2H), 0.99 (d, J=7.0 Hz, 6H); LC-MS (214 nm) >98%, 313.2 [M+H].

Provenance & Evidence