Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | (RS)-(4-cyano-phenylamino)-[5-ethoxy-2-fluoro-3-[(R)-tetrahydro-furan-3-yloxy]-phenyl]-acetic acid ethyl ester | HCID 70002924 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178472667 | HCID 178472667 | 80.1% |
Reaction Steps
To a mixture of 8.85 g (RS)-(4-cyano-phenylamino)-[5-ethoxy-2-fluoro-3-[(R)-tetrahydro-furan-3-yloxy]-phenyl]-acetic acid ethyl ester described in example 3.6 in 515 ml EtOH were added 20.21 g hydroxylamine hydrochloride and 81.1 ml triethylamine. The solution was stirred over night at 50° C., then evaporated. The crude product was isolated by extraction with EtOAc, then purified by chromatography on silica gel (CH2Cl2/MeOH) to yield 7.64 g (RS)-[5-ethoxy-2-fluoro-3-[(R)-tetrahydro-furan-3-yloxy]-phenyl]-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid ethyl ester as a light brown amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06548694B2 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-3b7b268995064b8a9f0becefb20742a7 |
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| Source note | uspto-grants-2003_04 |
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