Hydrochloric Acid → 13-cyclohexyl-6-(morpholine-4-carbonyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (200 μL, 0.2 mmol) was added to a solution of the preceding methyl ester (60 mg, 0.127 mmol) in methanol (1.2 mL) and tetrahydrofuran (1.2 mL) in a microwave vial. The vial was sealed and the contents heated at 90° C. for 10 min in a microwave apparatus, at which time the vial was cooled and additional NaOH was added (200 μL, 0.2 mmol). The solution was heated for another 5 min at 90° C. when LC/MS showed complete hydrolysis of the ester. The solution was acidified with dilute hydrochloric acid to precipitate the crude acid. The solid was collected and purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave the titled compound as a colorless solid (50 mg, 83%). ESI-MS m/z 473 (MH+), 1H NMR (500 MHz, CD3OD) δ 1.24–1.35 (m, 1 H), 1.40–1.55 (m, 2 H), 1.60–1.68 (m, 1 H), 1.77–2.22 (m, 6 H), 2.76 (m, 1 H), 2.88–3.04 (m, 1 H), 3.44–3.51 (m, 1 H), 3.58–3.93 (m, 9 H), 4.47–4.59 (m, 1 H), 4.89 (m, 1 H), 7.31–7.43 (m, 1 H), 7.47 (m, 3 H), 7.72 (m, 1 H), 7.88 (m, 1 H), 8.16 (m, 1 H).

Provenance & Evidence