Water → HCID 86696588, compound

HRID 1478354Notes

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 MeOH (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 MeOH was removed in vacuum. 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 DCM (3×4 mL). The organic layers were concentrated to afford the title compound as a yellow solid (29 mg, 69%).

Workup

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

Sources & evidence

ORD record: ord-0cd4edf0d62640a3ae6c5e4de917eebf
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403818B2

Reaction notes

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