Sodium Bicarbonate → HCID 77690288, Verbindung

HRID 2253415

Reaktionsgleichung

Reaktionsgleichung von HRID 2253415
C([Li])CCC.O1[C@@H:22]2[C@@:7]1([CH3:42])[CH:8]=[CH:9][C:10](=[O:41])[C@H:11]([CH3:40])[C@H:12]([OH:39])[C@@H:13]([CH3:38])[C:14](=[O:37])[C:15]([CH3:36])([CH3:35])[C@@H:16]([OH:34])[CH2:17][C:18](=[O:33])[N:19]([CH3:32])[C@H:20]([C:23]([CH3:31])=[CH:24][C:25]1[N:26]=[C:27]([CH3:30])[S:28][CH:29]=1)[CH2:21]2.C([O-])(O)=O.[Na+]>O1CCCC1.CCCCCC.O.[W](Cl)(Cl)(Cl)(Cl)(Cl)Cl>[OH:34][CH:16]1[C:15]([CH3:36])([CH3:35])[C:14](=[O:37])[CH:13]([CH3:38])[CH:12]([OH:39])[CH:11]([CH3:40])[C:10](=[O:41])[CH:9]=[CH:8][CH:7]([CH3:42])[CH2:22][CH2:21][CH:20]([C:23]([CH3:31])=[CH:24][C:25]2[N:26]=[C:27]([CH3:30])[S:28][CH:29]=2)[N:19]([CH3:32])[C:18](=[O:33])[CH2:17]1

Komponenten

8

Edukt 3

HCID 516892Sodium BicarbonateHCID 86587666HCID 86587666, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 77690288HCID 77690288, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83301Tungsten hexachlorideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of tungsten hexachloride (0.76 g) in tetrahydrofuran (20 mL) at −78° C. is treated with a 1.6 M solution of n-butyllithium in hexane (2.5 mL). The mixture is allowed to warm to ambient temperature over 20 minutes. A 13.8 mL portion of the resulting green solution is added to a solution of (4S,7R,8S,9R, 13R, 14S, 16S)-13,14-epoxy-4,8-dihydroxy-2,6,10-trioxo-1,5,5,7,9,13-hexamethyl-16-(1-(2-methylthiazol-4-yl)propen-2-yl)-1-aza-11-cyclohexadecene (370 mg) in 2 mL of tetrahydrofuran at ambient temperature. After 30 min, the reaction is cooled to 0° C. and treated with sat. NaHCO3 (10 mL). The mixture is diluted with water and extracted with CH2Cl2. The extract is dried over Na2SO4, filtered, and evaporated. The product is purified by flash chromatography on SiO2.

Aufarbeitung

  1. temperaturethe reaction is cooled to 0° C.
  2. extractionextracted with CH2Cl2
  3. dry with materialThe extract is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe product is purified by flash chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-f3f9a1ab971a4523ac22436db8578795
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323573B2

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