Diisopropylethylamine → 5-Chloro-pyridine-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide
Reaktionsgleichung
C(OC(=O)[NH:7][C@@H:8]1[CH2:14][C:13]([F:16])([F:15])[CH2:12][CH2:11][N:10]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[O:26][CH3:27])[C:9]1=[O:28])(C)(C)C.Cl.O1CCOCC1.CCN(C(C)C)C(C)C.[Cl:46][C:47]1[CH:48]=[CH:49][C:50]([S:53](Cl)(=[O:55])=[O:54])=[N:51][CH:52]=1>ClCCl>[CH3:27][O:26][C:19]1[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=1[CH2:17][N:10]1[CH2:11][CH2:12][C:13]([F:15])([F:16])[CH2:14][C@@H:8]([NH:7][S:53]([C:50]2[CH:49]=[CH:48][C:47]([Cl:46])=[CH:52][N:51]=2)(=[O:55])=[O:54])[C:9]1=[O:28]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
[(R)-1-(2,4-Dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (0.46 g, 1.0 mmol) was dissolved in 20 ml dichloromethane. 4 M HCl/1,4-dioxan (20 ml) were added dropwise and the mixture was allowed to react for 1 h. The reaction mixture was concentrated under reduced pressure and concentrated once from acetonitrile. To the resultant hydrochloride salt was added CH2Cl2 (15 ml) followed by the dropwise addition of Hünig's base (0.44 ml, 2.5 mmol). A solution of 5-chloropyridine-2-sulfonyl chloride (0.33 g, 1.1 mmol) in CH2Cl2 (5 ml) was added and the reaction mixture (pH 8) was stirred for a further 1.5 h. The reaction mixture was purified over silica gel (heptane-ethylacetate, 95:5-0:100): white solid 0.37 g (76%);
Aufarbeitung
- customto react for 1 h
- concentrationThe reaction mixture was concentrated under reduced pressure
- concentrationconcentrated once from acetonitrile
- additionTo the resultant hydrochloride salt was added CH2Cl2 (15 ml)
- customThe reaction mixture was purified over silica gel (heptane-ethylacetate, 95:5-0:100)
Quellen und Nachweise
- ORD-Eintrag
- ord-9a3793eb74b648518e3d9254a1bc78bb
- Quelldatensatz
- uspto-grants-2009_03
- Patentnummer
- US07501406B2
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