Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Boron Trichloride | HCID 25135 | — |
| Reactant | HCID 66701158 | HCID 66701158 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 58370274 | HCID 58370274 | 94.1% |
Reaction Steps
To a stirred solution of 0.107 g of 2-{[5-fluoro-1-(methoxymethoxyl)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester in 3 ml of dichloromethane at −65 to −70° C. was added by syringe 0.344 ml of 1M BCl3 in dichloromethane. The mixture was stirred for 10 minutes at −65 to −70° C. after which it was allowed to warm to RT and stirred at RT for 0.5 h. The mixture was poured into brine, extracted twice with ethyl acetate, dried, filtered and concentrated to an oil, which was chromatographed on silica gel eluting with ethyl acetate/dichloromethane/heptane to provide 0.088 g of 2-{[5-fluoro-1-(hydroxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07919628B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-df0a870165fc4ab2bc25269b6a34cf1b |
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| Source note | uspto-grants-2011_04 |
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