1-Hydroxybenzotriazole → (4R)-4-(4-fluoro-3-methylphenyl)-4-methoxy-N-(tetrahydro-2H-pyran-2-yloxy)butanamide
Reaktionsgleichung
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH2:8].C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+].[F:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]([O:37][CH3:38])[CH2:32][CH2:33][C:34](O)=[O:35])=[CH:27][C:26]=1[CH3:39].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]([O:37][CH3:38])[CH2:32][CH2:33][C:34]([NH:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[O:35])=[CH:27][C:26]=1[CH3:39]Komponenten
7
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
To a mixture of O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (175 mg, 1.5 mmol), HOBt (810 mg, 6.0 mmol), NaHCO3 (1.0 g, 11.9 mmol) and the crude (R)-4-(4-fluoro-3-methylphenyl)-4-methoxybutanoic acid in 60 mL CH2Cl2 was added EDC.HCl (958 mg, 5.0 mmol). The mixture was stirred for 3 h at 25° C. The solvent was removed under reduced pressure and the product isolated by flash column chromatography, eluting with 10% to 60% Ethyl acetate/Hexane gradient solvent to give 208 mg of the title compound.
Aufarbeitung
- customThe solvent was removed under reduced pressure
- customthe product isolated by flash column chromatography
- washeluting with 10% to 60% Ethyl acetate/Hexane gradient solvent
Quellen und Nachweise
- ORD-Eintrag
- ord-2081bd4068574f2c91fef1ab69070180
- Quelldatensatz
- uspto-grants-2012_02
- Patentnummer
- US08119692B2
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