Lithium Hydroxide → (1aRS,7bSR)-5-(4-fluoro-2-vinylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid

Lithium hydroxide (0.101 g) was added to a solution of methyl (1aRS,7bSR)-5-(4-fluoro-2-vinylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 75, 0.150 g) in a mixture of dioxane (3 mL) and water (0.6 mL) and the mixture was irradiated in the microwave at 130° C. for 30 minutes. After cooling, the mixture evaporated to dryness and the residue was acidified by addition of 10% aqueous citric acid (2 mL), extracted with DCM, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of methanol and DCM with a gradient of 0-10% to give (1aRS,7bSR)-5-(4-fluoro-2-vinylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid (0.0.35 g) as a glass.

1. customthe mixture was irradiated in the microwave at 130° C. for 30 minutes
2. temperatureAfter cooling
3. customthe mixture evaporated to dryness
4. additionthe residue was acidified by addition of 10% aqueous citric acid (2 mL)
5. extractionextracted with DCM
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customThe filtrate was evaporated to dryness
9. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and DCM with a gradient of 0-10%

ORD record

ord-06c98e3bcbbd463989e46689c38b6bf3

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290472B2