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p-Toluenesulfonic acid → 7alpha-(5-Acetoxypentyl)-11beta-fluoro-3-(tetrahydro-pyran-2-yloxy)oestra-1,3,5(10)-trien-17-one

HRID 1838883
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HRID 1838883 반응식
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([OH:28])[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][C@@H:19]2[F:29])([CH3:17])[C:15](=[O:30])[CH2:14][CH2:13]1)(=[O:3])[CH3:2].[O:31]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([O:28][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][O:31]3)[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][C@@H:19]2[F:29])([CH3:17])[C:15](=[O:30])[CH2:14][CH2:13]1)(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 699351197alpha-(5-Acetoxypentyl)-11beta-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one

생성물 1

HCID 229418067alpha-(5-Acetoxypentyl)-11beta-fluoro-3-(tetrahydro-pyran-2-yloxy)oestra-1,3,5(10)-trien-17-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

8.2 g of 7α-(5-acetoxypentyl)-11β-fluoro-3-hydroxyestra-1,3,5(10)-trien-17-one in 86 ml of THF are stirred at RT for 2.5 h with 8.6 ml of 3,4-dihydro-2H-pyran and 820 mg of p-toluenesulphonic acid. 0.5 ml of triethylamine is then added, and the mixture is diluted with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated in vacuo. After chromatographing the crude product on silica gel using a hexane-ethyl acetate gradient, 7.8 g of 7α-(5-acetoxypentyl)-11β-fluoro-3-(tetrahydropyran-2-yloxy) oestra-1,3,5(10)-trien-17-one are obtained as a foam.

후처리

  1. washwashed with saturated sodium chloride solution
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customare obtained as a foam

출처 및 근거

ORD 기록
ord-ed39373d1a6c4c849c806b71b5e43187
출처 데이터셋
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06677324B1

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