Dehydroepiandrosterone → 7-Oxodehydroepiandrosterone 3-acetate

HRID 650701

反応式

HRID 650701 の反応式
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[C:22]([O:26]O)(C)(C)[CH3:23].Cl[O-:29].[Ca+2].Cl[O-]>C(OCC)(=O)C>[C:22]([O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][C:12](=[O:29])[C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:19]1)(=[O:26])[CH3:23]

参加物

5

反応物 3

HCID 5881DehydroepiandrosteroneHCID 6410tert-Butyl hydroperoxideHCID 24504Calcium hypochlorite

生成物 1

HCID 97982297-Oxodehydroepiandrosterone 3-acetate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
10 °C

実験手順

DHEA-Ac (1.1 gm., 0.0033 mol.) was dissolved in a mixture of ethyl acetate (10 ml) and tert-butyl hydroperoxide (70% aqueous solution from Aldrich, 2.0 ml, 0.015 mol). The mixture was stirred at 10° C. and solid calcium hypochlorite (0.65 gm.) was added in small portions during a period of seven hours. The aqueous layer was then separated and the organic layer was stirred with sodium sulfite solution (3.0 gm in 10 ml of water) for 3 hours at 40-45° C. and filtered over celite. The aqueous yellow layer was removed and the organic layer was washed with half saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated on a rotary evaporator. The crude product, crystallized from methanol, afforded 3β-acetoxyandrost-5-en-7,17-dione (3) as a white solid, weight 0.42 gm.

後処理

  1. customThe aqueous layer was then separated
  2. stirringthe organic layer was stirred with sodium sulfite solution (3.0 gm in 10 ml of water) for 3 hours at 40-45° C.
  3. filtrationfiltered over celite
  4. customThe aqueous yellow layer was removed
  5. washthe organic layer was washed with half saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated on a rotary evaporator
  8. customThe crude product, crystallized from methanol

出典と根拠

ORDレコード
ord-5c26d26ae3c84689a0b3c18690d632d3
出典データセット
uspto-grants-2001_08
特許番号
US06274746B1

関連ノート

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