Water → 7-O-(Triethylsilyl)-10-deacetyl Baccatin III

HRID 1587240

반응식

HRID 1587240 반응식
[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([OH:39])[C:5]([C@@:7]1([CH3:38])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][C@@H:8]1[OH:37])=[O:6].[CH2:40]([Si:42](Cl)([CH2:45][CH3:46])[CH2:43][CH3:44])[CH3:41].C(OCC)(=O)C.O>N1C=CC=CC=1>[CH3:41][CH2:40][Si:42]([O:37][C@@H:8]1[C@@:7]2([CH3:38])[C:5]([C@H:4]([OH:39])[C:3]3[C:15]([CH3:16])([CH3:17])[C@:14]([OH:21])([C@@H:13]([O:22][C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:24])[C@@H:12]2[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9]1)[CH2:18][C@H:19]([OH:20])[C:2]=3[CH3:1])=[O:6])([CH2:45][CH3:46])[CH2:43][CH3:44]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 13819ChlorotriethylsilaneHCID 15427210-deacetylbaccatin III

생성물 1

HCID 117349827-O-(Triethylsilyl)-10-deacetyl Baccatin III수율 78%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

544 mg (1 mmol) of 10-deacetylbaccatine III, dissolved in 50 cm3 of anhydrous pyridine, are introduced under an argon atmosphere into a 100-cm3 round-bottomed flask equipped with a magnetic stirrer. 3.36 cm3 (3.014 g; 20 mmol) of triethylsilyl chloride are then added. The homogeneous, yellow reaction mixture is then stirred for 24 hours at 0° C. Ethyl acetate and water are then added. After settling has taken place, the separated aqueous phase is extracted with ethyl acetate. The combined organic phases are treated with saturated aqueous copper sulphate solution until the pyridine has been completely removed. The organic phases are washed with water and then with saturated sodium chloride solution, and then dried over anhydrous sodium sulphate. After filtration and evaporation of the solvents under reduced pressure, 2.73 g of a product are obtained, and this is purified on a silica column, eluting with a dichloromethane/methanol (99:1 by volume) mixture. 512 mg (0.778 mmol) of 10-deacetyl-7-triethylsilylbaccatine III are thereby obtained, in a 78% yield, in the form of a white solid, the characteristics of which are as follows:

후처리

  1. additionare introduced under an argon atmosphere into a 100-cm3 round-bottomed flask
  2. customequipped with a magnetic stirrer
  3. extractionthe separated aqueous phase is extracted with ethyl acetate
  4. additionThe combined organic phases are treated with saturated aqueous copper sulphate solution until the pyridine
  5. customhas been completely removed
  6. washThe organic phases are washed with water
  7. dry with materialwith saturated sodium chloride solution, and then dried over anhydrous sodium sulphate
  8. filtrationAfter filtration and evaporation of the solvents under reduced pressure, 2.73 g of a product
  9. customare obtained
  10. customthis is purified on a silica column
  11. washeluting with a dichloromethane/methanol (99:1 by volume) mixture

출처 및 근거

ORD 기록
ord-7f9a7c8d6c7049fcbf94c4d22af5457d
출처 데이터셋
uspto-grants-1993_06
특허 번호
USRE034277

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