Hydrochloric Acid → HCID 45280222, compound

Participants

Reaction Steps

To a solution of methyl({2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl}oxy)acetate (0.51 g, 1.25 mmol) in tetrahydrofuran (4 mL) and water (1 mL) was added lithium hydroxide (0.05 g, 1.62 mmol). The reaction mixture was stirred at ambient temperature for 16 h. To the reaction mixture was added 1 N HCl to adjust pH<2, then extracted with ethyl acetate (2×50 mL). The combined organic solution was washed with water and brine, then dried over sodium sulfate, filtered and concentrated to afford ({2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl}oxy)acetic acid (0.42 g, 85%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.33-7.26 (m, 1H), 7.15-7.00 (m, 3H), 6.64 (d, J=8.4 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 6.40-6.34 (m, 1H), 4.96 (d, J=9.0 Hz, 1H), 4.70 (d, J=9.0 Hz, 1H), 4.59 (s, 2H), 4.35-4.24 (m, 1H), 3.99-3.68 (m, 4H), 2.10-1.86 (m, 3H), 1.79-1.65 (m, 1H); MS (ES+) m/z 396.0 (M+1), 417.9 (M+23).

Provenance & Evidence