Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 68093200 | HCID 68093200 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 56656136 | HCID 56656136 | 21.5% |
Reaction Steps
A mixture of methyl 7-[2-((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 46, 0.096 g) and lithium hydroxide monohydrate (0.168 g) in water (0.8 mL) and dioxane (3.2 mL), was sealed in a microwave vial and irradiated in the microwave at 135° C. for 45 minutes. After cooling, the mixture was diluted with ethanol, acidified with formic acid and evaporated to dryness. The residue was triturated with 10% methanol in DCM, filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with DMAW 350. The product was azeotroped with toluene and ethanol and the residue was triturated with ethyl acetate to give 7-[2-((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylic acid (0.020 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266896B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-aba619231765496a8a4254e6983e149b |
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| Source note | uspto-grants-2016_02 |
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