Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium | HCID 5462222 | — |
| Reactant | HCID 58563043 | HCID 58563043 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 58563092 | HCID 58563092 | 37.4% |
Reaction Steps
To a solution of N—[(S)-1-(5-bromo-2-fluoro-phenyl)-3-hydroxy-1,3-dimethyl-butyl]-2-chloro-acetamide (intermediate A15A) (3.11 g, 8.5 mmol) in toluene (150 ml) at 23° C. was added dropwise a solution of potassium amylate (1.7 M in toluene; 25.0 ml, 42 mmol) within 10 min (slightly exothermic). The light brown solution was stirred at 23° C. for 2 h. Diluted with water, 1N HCl and brine and extracted twice with ethyl acetate. The organic layers were washed with sat. NaHCO3 solution and brine, dried over Na2SO4, filtered and evaporated to give a light brown oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound as an off-white solid (1.05 g, 37%). MS (ISP): m/z=330.0 [(M+H)+] and 332.0 [(M+2+H)+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08748418B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-be6190ba10a54886a0c3b745e5e5a8c0 |
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| Source note | uspto-grants-2014_06 |
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