Benzyl mercaptan → 21-Benzylthio-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1077009노트

반응식

HRID 1077009 반응식
[C:1]1([CH2:7][SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Br[CH2:11][C:12](=[O:34])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([C:28](=[O:32])[CH2:29]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][C@H:22]([OH:33])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1>CC(O)C.C1(C)C=CC=CC=1>[CH2:7]([S:8][CH2:11][C:12](=[O:34])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([C:28](=[O:32])[CH2:29]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][C@H:22]([OH:33])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 7509Benzyl mercaptanHCID 5360545SodiumHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

생성물 1

HCID 8673346821-Benzylthio-3alpha-hydroxy-5alpha-pregnane-11,20-dione

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3776Isopropanol용매

실험 절차

Toluene-α-thiol (1.0 ml.) was added to a warm solution of sodium (0.6 g.) in a mixture of propan-2-ol (25 ml.) and toluene (30 ml.). 21-Bromo-3α-hydroxy-5α-pregnane-11,20 -dione (0.7 g.) was then added and the mixture was gently refluxed for 2 hr. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was purified by preparative t.l.c. (CHCl3) to give title compound (0.4 g.) as a white foam, [α]D + 89° (c 1.1).

후처리

  1. temperaturethe mixture was gently refluxed for 2 hr
  2. customThe mixture was then partitioned between water and ether
  3. washthe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by preparative t.l.c

출처 및 근거

ORD 기록
ord-be45fe49846a4b849ed0a10e61235ffb
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959260

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