Reaktionsgleichung
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([C@@H:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13])=[CH:8][CH:7]=2)[CH2:3]1.CS(Cl)(=O)=O.[F:23][C:24]1[C:29]([F:30])=[C:28]([CH3:31])[CH:27]=[CH:26][C:25]=1O.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CC(N(C)C)=O.O>[F:23][C:24]1[C:29]([F:30])=[C:28]([CH3:31])[CH:27]=[CH:26][C:25]=1[O:1][CH:2]1[CH2:3][N:4]([C:6]2[CH:7]=[CH:8][C:9]([C@@H:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13])=[CH:10][CH:11]=2)[CH2:5]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To 0.023 g (0.10 mmol) (S)—N-{1-[4-(3-hydroxy-azetidin-1-yl)-phenyl]-ethyl}-acetamide (V.1) in 5 mL THF are added 0.017 mL (0.12 mmol) TEA and the mixture is cooled to 0° C. 0.008 mL (0.10 mmol) methanesulfonyl chloride are added dropwise and the mixture is stirred for 2 h at 0° C. Water is added and the aq. phase is extracted with ethyl acetate (2×). The combined organic layers are dried (MgSO4) and concentrated. The residue is taken up in 1.0 mL DMA and is added to a mixture of 0.014 g (0.12 mmol) 2,3-difluoro-4-methylphenol and 0.039 g (0.12 mmol) Cs2CO3 in 1.0 mL DMA. The resulting mixture is stirred for 12 h at 100° C. After cooling the mixture is directly purified by HPLC (MeOH/water (+0.1% NH4OH)) to yield the desired product.
Aufarbeitung
- extractionthe aq. phase is extracted with ethyl acetate (2×)
- dry with materialThe combined organic layers are dried (MgSO4)
- concentrationconcentrated
- stirringThe resulting mixture is stirred for 12 h at 100° C
- temperatureAfter cooling the mixture
- customis directly purified by HPLC (MeOH/water (+0.1% NH4OH))
Quellen und Nachweise
- ORD-Eintrag
- ord-61c7ced06ea8445ebbf1b886e10cbb3f
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08530461B2
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