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

HRID 1903000
ノート
印刷プレビュー

反応式

HRID 1903000 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
-40 °C

実験手順

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 solution 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.

後処理

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

出典と根拠

ORDレコード
ord-9f6eb3123446479288bee69076f69062
出典データセット
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04435326

反応ノート

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