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Methanol → Osaterone

HRID 2231994
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HRID 2231994 반응식
C([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[O:18][CH2:19]2)[C:14]([Cl:28])=[CH:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=O)C.CO.C[O-].[Na+].O1CCCC1>O>[Cl:28][C:14]1[C:15]2[C@:20]([CH3:21])([CH2:19][O:18][C:17](=[O:27])[CH:16]=2)[C@@H:22]2[C@H:12]([C@H:11]3[C@:25]([CH3:26])([CH2:24][CH2:23]2)[C@@:5]([OH:4])([C:6](=[O:8])[CH3:7])[CH2:9][CH2:10]3)[CH:13]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 887Methanol2회HCID 8028TetrahydrofuranHCID 114992(4aR,4bS,6aS,7R,9aS,9bR)-7-Acetyl-7-(acetyloxy)-11-chloro-4a,4b,5,6,6a,7,8,9,9a,9b-decahydro-4a,6a-dimethylcyclopenta(5,6)naphtho(1,2-c)pyran-2(4H)-oneHCID 10942334Sodium Methoxide

생성물 1

HCID 3047806Osaterone

시약·촉매·용매 1

HCID 962
Water
용매

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온도
70 °C

실험 절차

A mixture of 116 mg iof 17α-acetoxy-6-chloro-2-oxapregna-4,6-diene-3,20-dione, 0.5 ml of an about 28% methanol solution of sodium methylate, 0.1 ml of tetrahydrofuran and 5 ml of methanol was heated at 70° C. for 10 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a 30% aqueous solution of hydrogen chloride and then with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by TLC [developing solvent: chloroform/acetone (19/1)] to give 70 mg of 6-chloro-17α-hydroxy-2-oxapregna-4,6-diene-3,20-dione.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a 30% aqueous solution of hydrogen chloride
  3. dry with materialwith a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by TLC [developing solvent: chloroform/acetone (19/1)]

출처 및 근거

ORD 기록
ord-9ecddbe23f4349dda0d1aa4955ab27b2
출처 데이터셋
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04785103

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