Sodium Hydroxide → (1S,1aS,6bR)-5-((7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-4-yl)oxy)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylic acid

HRID 920115Notes

Reaction equation

[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][CH:7]=[C:6]([O:12][C:13]3[CH:14]=[CH:15][C:16]4[O:20][C@@H:19]5[C@@H:21]([C:22]([O:24]CC)=[O:23])[C@@H:18]5[C:17]=4[CH:27]=3)[C:5]=2[CH2:4][CH2:3]1.[OH-].[Na+]>C1COCC1.CO>[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][CH:7]=[C:6]([O:12][C:13]3[CH:14]=[CH:15][C:16]4[O:20][C@@H:19]5[C@@H:21]([C:22]([OH:24])=[O:23])[C@@H:18]5[C:17]=4[CH:27]=3)[C:5]=2[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of ester product of Step A (360 mg, 0.98 mmol) in THF (3 mL) and methanol (3 mL) was added sodium hydroxide aqueous solution (1 mL, 2 M, 2 mmol) at room temperature. The mixture was stirred at 60° C. for 2 hrs. The solvent was removed under reduced pressure and the residue was dissolved into water (5 mL). The solution was neutralized with HCl (2 mol/L) to pH=7 and white solid precipitated out of solution. The white solid was collected by filtration and dried in air to give the title compound (230 mg, 69.3%).

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved into water (5 mL)
customprecipitated out of solution
filtrationThe white solid was collected by filtration
customdried in air

Sources & evidence

ORD record: ord-929ccc51f7bb4d359add50b736a192eb
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273046B2

Reaction notes

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