p-Toluenesulfonic acid → 17beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal

HRID 1834913노트

반응식

HRID 1834913 반응식
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])[CH2:10][CH2:9]3.[CH:24](S)([SH:26])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[CH2:25]1[O:23][C:13]2([CH2:14][C@H:15]([CH3:22])[C@@:16]3([CH2:17][OH:18])[C:11]([CH2:10][CH2:9][C@@H:8]4[C@@H:19]3[CH2:20][CH2:21][C@@:3]3([CH3:4])[C@H:5]4[CH2:6][CH2:7][C@@H:2]3[OH:1])=[CH:12]2)[S:26][CH2:24]1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 336451,1-EthanedithiolHCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one

생성물 1

HCID 2279742417beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

17β,19-Dihydroxy-1α-methyl-4-androsten-3-one in acetic acid is treated with ethanedithiol and p-toluenesulfonic acid. After standing about 4 hours at room temperature, the solution is poured onto water and the mixture extracted with methylenechloride. The methylenechloride extract is washed well with water, sodium hydroxide solution, water, dried over sodium sulfate and evaporated under reduced pressure to leave 17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal which is recrystallized once from acetone-hexane.

후처리

  1. additionthe solution is poured onto water
  2. extractionthe mixture extracted with methylenechloride
  3. extractionThe methylenechloride extract
  4. washis washed well with water, sodium hydroxide solution, water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-be57ad11a4a4418a932f8ae6b986875e
출처 데이터셋
uspto-grants-1978_01
특허 번호
US04071624

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