Potassium Hydroxide → HCID 68504155, compound

HRID 1714055Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37]C)=[O:36])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([C:22](=[O:29])[CH2:23][N:24]4[CH:28]=[CH:27][N:26]=[CH:25]4)[CH2:18][C:17]4[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>O1CCOCC1.O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([OH:37])=[O:36])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([C:22](=[O:29])[CH2:23][N:24]4[CH:28]=[CH:27][N:26]=[CH:25]4)[CH2:18][C:17]4[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 14-cyclohexyl-3-fluoro-6-(1H-imidazol-1-ylacetyl)-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate was dissolved in a solution of dioxane: H2O (1:1) (0.1 M) and to that solution aqueous KOH (3 eq, 5 N) were added. The solution was stirred at 60° C. for 3 h. The solvent was evaporated in vacuo. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (41%).

Workup

additionwere added
customThe solvent was evaporated in vacuo
customThe crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
additionFractions containing the pure compound
customfreeze dried

Sources & evidence

ORD record: ord-ffc51078977c462789be17ed77a2315d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795247B2

Reaction notes

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