Hydrochloric Acid → Methyl (+/-)-13-cyclohexyl-6,7-dihydro-6-carboxy-6-fluoro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 1394902Notes

Reaction equation

[OH-].[Na+].[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:32]([O:34][CH3:35])=[O:33])=[CH:14][C:15]=3[N:16]3[CH2:22][C:21]([C:24]([O:26]C)=[O:25])([F:23])[CH2:20][C:19]4[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=4[C:17]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl>CO.O1CCCC1>[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:32]([O:34][CH3:35])=[O:33])=[CH:14][C:15]=3[N:16]3[CH2:22][C:21]([C:24]([OH:26])=[O:25])([F:23])[CH2:20][C:19]4[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=4[C:17]=23)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

Conditions

Temperature: 65 °C

Procedure

Sodium hydroxide (50 μL of 1N, 0.05 mmol) was added to a solution of methyl (±)-13-cyclohexyl-6,7-dihydro-6-carbomethoxy-6-fluoro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (12.0 mg, 0.027 mmol) in methanol (0.5 mL) and tetrahydrofuran (0.5 mL) in a microwave vial. The vial was sealed and the contents heated at 65° C. for 20 min in a microwave apparatus. The solution was acidified with dilute hydrochloric acid to precipitate the crude acid. The solid was collected and was purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave the titled compound as a white solid (10 mg, 85%). ESI-MS m/z 436 (MH+).

Workup

customThe vial was sealed
customto precipitate the crude acid
customThe solid was collected
customwas purified on the Shimadzu preparative liquid chromatograph
additionThe product containing fraction
concentrationwas concentrated on a Speed Vac®

Sources & evidence

ORD record: ord-9643b30bca92480f99c43d63d57220b1
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348425B2

Reaction notes

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