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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 920115Generated: October 31, 2026

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

https://huagongshe.com/reaction/920115

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
Reactant(1S,1aS,6bR)-ethyl 5-((7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-4-yl)oxy)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylateHCID 89670276—
SolventMethanolHCID 887—
SolventTetrahydrofuranHCID 8028—
Product(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 acidHCID 11780678569.4%

Reaction Conditions

Temperature60 °C

Reaction Steps

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%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09273046B2
Source datasetuspto-grants-2016_03
ORD IDord-929ccc51f7bb4d359add50b736a192eb
Source noteuspto-grants-2016_03