Methanethiol → 17alpha-Methylthio-1,4-Androstadiene-3,11-Dione

HRID 2052255노트

반응식

HRID 2052255 반응식
[Na].[CH3:2][SH:3].CS(O[C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([C:26](=[O:28])[CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C:18](=[CH:19][C:20](=[O:29])[CH:21]=[CH:22]1)[CH2:17][CH2:16]3)(=O)=O>C(O)C>[CH3:2][S:3][C@@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([C:26](=[O:28])[CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C:18](=[CH:19][C:20](=[O:29])[CH:21]=[CH:22]1)[CH2:17][CH2:16]3

참가 물질

5

반응물 3

HCID 878MethanethiolHCID 5360545SodiumHCID 5660910317beta-Methanesulfonyloxy-1,4-androstadiene-3,11-dione

생성물 1

HCID 5435815917alpha-Methylthio-1,4-Androstadiene-3,11-Dione

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

To 6.9 gm. of sodium metal dissolved in 225 ml. of ethanol is added 30 ml. of methylmercaptan followed by 10 gm. of 17β-methanesulfonyloxy-1,4-androstadiene-3,11-dione. Heat at reflux for 18 hours. Cool the solution to 0° C., filter solids and crystallize from chloroform/hexane to obtain the title compound; m.p. 180°-183° C.; [α]D26 +101.6° (DMF).

후처리

  1. temperatureHeat
  2. temperatureat reflux for 18 hours
  3. filtrationfilter solids
  4. customcrystallize from chloroform/hexane

출처 및 근거

ORD 기록
ord-4d72ea8ffee140d8805e2f915f730ea0
출처 데이터셋
uspto-grants-1980_01
특허 번호
US04183924

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