Acetic Anhydride → 7-O-(Triethylsilyl) Baccatin III

HRID 619703

Reaktionsgleichung

Reaktionsgleichung von HRID 619703
[CH2:1]([Si:3](Cl)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:9][C:10]1[C@@H:27]([OH:28])[CH2:26][C@:22]2([OH:29])[C:23]([CH3:25])([CH3:24])[C:11]=1[C@@H:12]([OH:47])[C:13]([C@@:15]1([CH3:46])[C@H:20]([C@@H:21]2[O:30][C:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:32])[C@:19]2([O:41][C:42]([CH3:44])=[O:43])[CH2:39][O:40][C@@H:18]2[CH2:17][C@@H:16]1[OH:45])=[O:14].[C:48](OC(=O)C)(=[O:50])[CH3:49]>N1C=CC=CC=1>[CH3:2][CH2:1][Si:3]([O:45][C@@H:16]1[C@@:15]2([CH3:46])[C:13]([C@H:12]([O:47][C:48]([CH3:49])=[O:50])[C:11]3[C:23]([CH3:24])([CH3:25])[C@:22]([OH:29])([C@@H:21]([O:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:32])[C@@H:20]2[C@:19]2([O:41][C:42]([CH3:44])=[O:43])[CH2:39][O:40][C@@H:18]2[CH2:17]1)[CH2:26][C@H:27]([OH:28])[C:10]=3[CH3:9])=[O:14])([CH2:6][CH3:7])[CH2:4][CH3:5]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 13819ChlorotriethylsilaneHCID 15427210-deacetylbaccatin III

Produkt 1

HCID 99399277-O-(Triethylsilyl) Baccatin IIIAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

182 g of triethylsilyl chloride are added over 1 hour 20 minutes to a solution of 293.9 g of 10-deacetylbaccatin III in 2.7 liters of pyridine. The solution obtained is stirred for 40 hours at 5° C. 360 g of acetic anhydride are then added while the temperature is maintained at 5° C. The suspension obtained is stirred for 48 hours at 20° C. and then poured into 40 liters of ice-cold water. The precipitate obtained is separated by filtration, then washed with 8 times 2 liters of water and lastly dissolved in 3 liters of ethyl acetate. The organic phase is dried over magnesium sulphate. After filtration and concentration under reduced pressure, the product obtained is crystallized in isopropyl ether. 7-(Triethylsilyl)baccatin III is thereby obtained in a 77% yield, the characteristics of which product are as follows:

Aufarbeitung

  1. customThe solution obtained
  2. temperatureis maintained at 5° C
  3. customThe suspension obtained
  4. stirringis stirred for 48 hours at 20° C.
  5. customThe precipitate obtained
  6. customis separated by filtration
  7. washwashed with 8 times 2 liters of water
  8. dissolutionlastly dissolved in 3 liters of ethyl acetate
  9. dry with materialThe organic phase is dried over magnesium sulphate
  10. filtrationAfter filtration and concentration under reduced pressure
  11. customthe product obtained
  12. customis crystallized in isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-64b6443b641f4ba481be1bfbe1569598
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05959125

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