Sodium Hydroxide → 8-(4-((tert-butoxycarbonylamino)methyl)-3-fluorophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid

HRID 1854874Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 8-(4-((tert-butoxycarbonylamino)methyl)-3-fluorophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (24 mg, 0.050 mmol) was dissolved in methanol (2 mL) and 1M aqueous sodium hydroxide (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 and the residue was dissolved in water (5 mL) and neutralized with 1M HCl (˜0.5 mL). The precipitate formed was extracted with CH2Cl2 (3×4 mL). The organic layer was concentrated to afford the title compound as a yellow solid (20 mg, 86%). ESI-MS m/z: 3467 (M+H)+.

Workup

temperatureAfter cooling
customthe methanol was removed in vacuo
dissolutionthe residue was dissolved in water (5 mL)
customThe precipitate formed
extractionwas extracted with CH2Cl2 (3×4 mL)
concentrationThe organic layer was concentrated

Sources & evidence

ORD record: ord-45beef1ba67a43478ec4db39abcc3c57
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962842B2

Reaction notes

Loading…