Sodium Hydroxide → HCID 118112338, compound

Participants

Reaction Steps

(S)-3-(6-(4-fluorobenzyl)-1,3-dioxo-5,6,11,11a-tetrahydro-1H-imidazo[1′,5′:1,6]pyrido[3,4-b]indol-2(3H)-yl)propanoic acid (A) (40.35 g, 95.7 mmol) dissolved in tetrahydrofuran (960 mL) in 2 L round bottom flask equipped with addition funnel was degassed and cooled in ice water bath. 1M NaOH (86.2 mL, 86.2 mmol) was added dropwise over 3 hr at 0° C. The solvent removed under reduce pressure to afford (S)-3-(6-(4-fluorobenzyl)-1,3-dioxo-5,6,11,11a-tetrahydro-1H-imidazo[1′,5′:1,6]pyrido[3,4-b]indol-2(3H)-yl)propanoic acid sodium salt (Compound A sodium salt; 42.4 g, 100%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 7.53 (d, 1H), 7.47 (d, 1H), 7.16-7.02 (m, 6H), 5.40 (q, 2H), 4.89 (d, 1H), 4.36-4.28 (m, 2H), 3.56-3.49 (m, 2H), 3.27-3.20 (m, 1H), 2.76-2.67 (m, 1H), 2.17-2.11 (m, 2H); LC-MS [M+H+ 422].

Provenance & Evidence