Hydrochloric Acid → 6-{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}-13-cyclohexyl-3-methoxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1669434Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH3:41])[CH2:9][CH2:10][CH:11]1[CH2:17][C:16]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=2[C:14]2=[C:24]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[C:25]3[CH:26]=[CH:27][C:28]([C:31]([O:33]C)=[O:32])=[CH:29][C:30]=3[N:13]2[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1>[C:1]([O:5][C:6]([N:8]([CH3:41])[CH2:9][CH2:10][CH:11]1[CH2:17][C:16]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=2[C:14]2=[C:24]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[C:25]3[CH:26]=[CH:27][C:28]([C:31]([OH:33])=[O:32])=[CH:29][C:30]=3[N:13]2[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a 0.05M solution of methyl 6-{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}-13-cyclohexyl-3-methoxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate in dioxane, 1M aqueous KOH solution (10 eq) was added and the mixture was heated to 70° C. After 2 h the mixture was neutralised with 1N HCl and then all volatiles were removed in vacuo. The residue was taken up with DCM and filtered to remove salts. The crude material was used without purification in the next step. (ES+) m/z 547 (M+H)+.

Workup

customall volatiles were removed in vacuo
filtrationfiltered
customto remove salts
customThe crude material was used without purification in the next step

Sources & evidence

ORD record: ord-8642fb616d93455e82b268d198d02071
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989438B2

Reaction notes

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