19-Mercaptoandrost-4-ene-3,17-dione → 3-Fluoromethylene-19-mercapto-4-androsten-17-one

HRID 1650790노트

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HRID 1650790 반응식
F[B-](F)(F)F.[F:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[SH:33][CH2:34][C@@:35]12[C@@H:52]3[C@H:43]([C@H:44]4[C@@:48]([CH2:50][CH2:51]3)([CH3:49])[C:47](=[O:53])[CH2:46][CH2:45]4)[CH2:42][CH2:41][C:40]1=[CH:39][C:38](=O)[CH2:37][CH2:36]2>O1CCCC1.Cl>[F:6][CH:7]=[C:38]1[CH2:37][CH2:36][C@@:35]2([CH2:34][SH:33])[C:40]([CH2:41][CH2:42][C@@H:43]3[C@@H:52]2[CH2:51][CH2:50][C@@:48]2([CH3:49])[C@H:44]3[CH2:45][CH2:46][C:47]2=[O:53])=[CH:39]1

참가 물질

6

반응물 3

HCID 14614119-Mercaptoandrost-4-ene-3,17-dioneHCID 11303586(Fluoromethyl)triphenylphosphonium tetrafluoroborateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 540614093-Fluoromethylene-19-mercapto-4-androsten-17-one수율 47.7%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

17.2 g of fluoromethyl triphenylphosphonium tetrafluoroborate is suspended in 120 ml of tetrahydrofuran and mixed at 25° C. by portions with 7.8 g of potassium tert-butylate. Stirring is continued for one more hour, it is cooled to 0° C. and 1.5 g of 19-mercapto-4-androstene-3,17-dione (European patent 100,556) is instilled in 10 ml of tetrahydrofuran and stirring is continud for 30 more minutes. Then it is neutralized in 1N hydrochloric acid, the reaction mixture is added to waer, extracted 4 times with ethyl acetate, the organic phases washed neutral, dried on sodium sulfate and freed rom the solvent in a vacuum. After chromatography on silica gel with hexane/ethyl acetate, 752 mg of 3-fluoromethylene-19-mercapto-4-androsten-17-one with a melting point of 118°-120° C. is obtained.

후처리

  1. stirringstirring
  2. additionthe reaction mixture is added to waer
  3. extractionextracted 4 times with ethyl acetate
  4. washthe organic phases washed neutral
  5. customdried on sodium sulfate

출처 및 근거

ORD 기록
ord-1e8d401049194e2e9210c36950f06ec5
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04925834

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