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Hydrogen Sulfide → 17beta-Ethylthio-9-fluoro-11beta-hydroxy-17alpha-mercaptoandrosta-1,4-diene-3-one

HRID 543465
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HRID 543465 반응식
[CH2:1]([S:3][C:4]1[C@:5]2([CH2:22][C@H:21]([OH:23])[C@@:20]3([F:24])[C@@H:10]([CH2:11][CH2:12][C:13]4[C@:18]3([CH3:19])[CH:17]=[CH:16][C:15](=[O:25])[CH:14]=4)[C@@H:7]2[CH2:8][CH:9]=1)[CH3:6])[CH3:2].[SH2:26].B(F)(F)F.CCOCC>ClCCl.C(Cl)(Cl)Cl>[CH3:2][CH2:1][S:3][C@@:4]1([SH:26])[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@:20]([F:24])([C@@H:21]([OH:23])[CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH:16]=[CH:17]1)[CH2:12][CH2:11]3
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6

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HCID 402Hydrogen SulfideHCID 8000Boron trifluoride etherateHCID 1291771217-Ethylthio-9-fluoro-11beta-hydroxyandrosta-1,4,16-triene-3-one

생성물 1

HCID 1327444317beta-Ethylthio-9-fluoro-11beta-hydroxy-17alpha-mercaptoandrosta-1,4-diene-3-one

시약·촉매·용매 2

HCID 6212Chloroform용매
HCID 6344
Dichloromethane
용매

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온도
-40 °C

실험 절차

A solution of 2.0 g of 17-ethylthio-9-fluoro-11β-hydroxyandrosta-1,4,16-triene-3-one in dry dichloromethane (120 ml) was cooled and stirred in a bath at about -40° C. and a slow stream of hydrogen sulfide gas was passed into the solution while boron trifluoride etherate (1.2 ml) was added. After about 3.5 to 4.0 hours, the mixture was diluted with chloroform, warmed to room temperature and washed successively with a dilute sodium bicarbonate solution and water. The soluiton was dried (anhydrous magnesium sulfate), evaporated and the solid residue crystallized from ethyl acetate to afford 1.4. g of the title compound, melting point 239°-242° C.

후처리

  1. additionwas added
  2. temperaturewarmed to room temperature
  3. washwashed successively with a dilute sodium bicarbonate solution and water
  4. dry with materialThe soluiton was dried (anhydrous magnesium sulfate)
  5. customevaporated
  6. customthe solid residue crystallized from ethyl acetate
  7. customto afford 1.4

출처 및 근거

ORD 기록
ord-449562b410bc4fbd8e5e841defa7045c
출처 데이터셋
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04446071

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