Water → HCID 86696588, compound

HRID 1854877Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([C:19]3[CH:20]=[CH:21][N:22]4[C:27]([C:28]=3[CH3:29])=[C:26]([CH:30]3[CH2:32][CH2:31]3)[CH:25]=[C:24]([C:33]([O:35]C)=[O:34])[C:23]4=[O:37])=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:38])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([C:19]3[CH:20]=[CH:21][N:22]4[C:27]([C:28]=3[CH3:29])=[C:26]([CH:30]3[CH2:32][CH2:31]3)[CH:25]=[C:24]([C:33]([OH:35])=[O:34])[C:23]4=[O:37])=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:38])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 8-(3-(tert-butoxycarbonylamino)-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (43 mg, 0.083 mmol) was dissolved in methanol (2 mL) and sodium hydroxide 1M solution in water (0.5 mL, 0.5 mmol) was added. The mixture was stirred at 50° C. for 2 h. After cooling, the methanol was removed in vacuo. The residue was dissolved in water (5 mL) and then neutralized with 1M HCl (˜0.5 mL). The precipitate formed was stirred at room temperature overnight. The mixture was extracted with CH2Cl2 (3×4 mL). The organic layers were concentrated to afford the title compound as a yellow solid (29 mg, 69%). ESI-MS m/z: 504 (M+H)+.

Workup

temperatureAfter cooling
customthe methanol was removed in vacuo
dissolutionThe residue was dissolved in water (5 mL)
customThe precipitate formed
stirringwas stirred at room temperature overnight
extractionThe mixture was extracted with CH2Cl2 (3×4 mL)
concentrationThe organic layers were concentrated

Sources & evidence

ORD record: ord-55048492ab734466a1268c096af2a8e2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962842B2

Reaction notes

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