Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | (2-Ethoxyphenyl)boronic acid | HCID 2734902 | — |
| Edukt | (2R,3S,5R)-5-[(1S,2S)-1-hydroxy-2-acetylamino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester | HCID 68561702 | — |
| Katalysator | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | HCID 68563894 | HCID 68563894 | 46,4% |
Reaktionsschritte
Add 2-ethoxyphenylboronic acid (0.065 g, 0.394 mmol) and (1,1′-bis(diphenylphosphino)ferrocene) palladium(II) chloride (0.021 g) to a mixture of 2M sodium carbonate solution (0.262 g, 0.525 mmol) and (2R,3S,5R)-5-[(1S,2S)-1-hydroxy-2-acetylamino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester (0.151 g, 0.262 mmol) in tetrahydrofuran (2.62 mL) in a sealed tube flushed with nitrogen. Heat the tube at 80° C. for 3 days. Add saturated aqueous sodium chloride and extract with ethyl acetate (2×50 mL). Dry over magnesium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with hexanes containing 25-50% ethyl acetate to provide the title compound (0.075 g, 46%) as a white foam.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07745438B2 |
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| Quelldatensatz | uspto-grants-2010_06 |
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| ORD ID | ord-7469b8ee12ed4e0d8ea14153e71354df |
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| Quellennotiz | uspto-grants-2010_06 |
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