Reaktionsgleichung
[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH:12]([C:14]1[CH:26]=[CH:25][C:17]([C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1)O)(C(C)(C)C)(C)C.S(Cl)(Cl)=O.[CH3:34][C@H:35]1[CH2:40][NH:39][C@H:38]([CH3:41])[CH2:37][NH:36]1.O.[F-].C([N+](CC)(CC)CC)C>>[CH2:23]([N:20]([CH2:21][CH3:22])[C:18](=[O:19])[C:17]1[CH:16]=[CH:15][C:14]([C@@H:12]([N:36]2[CH2:37][C@H:38]([CH3:41])[NH:39][CH2:40][C@H:35]2[CH3:34])[C:11]2[CH:27]=[CH:28][CH:29]=[C:9]([OH:8])[CH:10]=2)=[CH:26][CH:25]=1)[CH3:24]Komponenten
5
Edukt 4
Produkt 1
Versuchsvorschrift
4-(3-(tert-Butyldimethylsilyloxy)-α-hydroxybenzyl)-N,N-diethylbenzamide (Example 1, infra) was treated with thionyl chloride and trans-2,5-dimethylpiperazine as described in Example 5. The crude mixture of diastereomers was purified by chromatography on silica gel (Waters Prep 500) with dichloromethane:ethanol:triethylamine (100:0.25:0.1). The less mobile isomer (1.28 g, 2.5 mmol) was dissolved in acetonitrile and treated with tetraethylammonium fluoride hydrate (0.6 g, 4.0 mmol) as in Example 7 to give 0.46 g of (±)-N,N-diethyl-4-((αR*)-3-hydroxy-α-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)benzyl)benzamide as a white solid, mp 175-177° C.
Aufarbeitung
- additionThe crude mixture of diastereomers
- customwas purified by chromatography on silica gel (Waters Prep 500) with dichloromethane:ethanol:triethylamine (100:0.25:0.1)
- dissolutionThe less mobile isomer (1.28 g, 2.5 mmol) was dissolved in acetonitrile
Quellen und Nachweise
- ORD-Eintrag
- ord-ea780c10ea604e4d81e3dc5ff792b861
- Quelldatensatz
- uspto-grants-2005_07
- Patentnummer
- US06919350B2
Verknüpfte Notizen
Wird geladen…