Sulfuric Acid → (17alpha)-17-Hydroxy-3-oxoandrosta-4,9(11)-diene-17-carbonitrile

HRID 1650076노트

반응식

HRID 1650076 반응식
S(=O)(=O)(O)O.[CH3:6][C@@:7]12[C:15]([OH:18])([C:16]#[N:17])[CH2:14][CH2:13][C@H:12]1[C@@H:11]1[CH2:19][CH2:20][C:21]3[C@@:27]([CH3:28])([C:10]1(O)[CH2:9][CH2:8]2)[CH2:26][CH2:25][C:23](=[O:24])[CH:22]=3>O>[C:16]([C@@:15]1([OH:18])[CH2:14][CH2:13][C@H:12]2[C@H:11]3[C:10](=[CH:9][CH2:8][C@:7]12[CH3:6])[C@:27]1([CH3:28])[C:21](=[CH:22][C:23](=[O:24])[CH2:25][CH2:26]1)[CH2:20][CH2:19]3)#[N:17]

참가 물질

4

반응물 2

HCID 1118Sulfuric Acid2회HCID 308277817-Cyano-9,17-dihydroxyandrost-4-ene-3-one

생성물 1

HCID 10859900(17alpha)-17-Hydroxy-3-oxoandrosta-4,9(11)-diene-17-carbonitrile

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A mixture of sulfuric acid (37 ml) and water (32.1 ml) is added to 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one (I, EXAMPLE 87, 13.28 g). The mixture is stirred at 20°-25° for 19 hr, stirred at 30° for 4 hr, then cooled to 10°. Sulfuric acid (11.2 ml) is added, the mixture is stirred at 20°-25° for 45 min, then cooled to 0° and water (55 ml) is added, maintaining the temperature at <5°. The product is collected by vacuum filtration and washed with water (80 ml), aqueous ammonium acetate (1M, 80 ml) and water (80 ml). The solid is dried in an air stream for 24 hr to give the title compound, mp 225°-228°.

후처리

  1. stirringstirred at 30° for 4 hr
  2. temperaturecooled to 10°
  3. stirringthe mixture is stirred at 20°-25° for 45 min
  4. temperaturecooled to 0°
  5. temperaturemaintaining the temperature at <5°
  6. filtrationThe product is collected by vacuum filtration
  7. washwashed with water (80 ml), aqueous ammonium acetate (1M, 80 ml) and water (80 ml)
  8. customThe solid is dried in an air stream for 24 hr

출처 및 근거

ORD 기록
ord-6f13b0dcdf62411ab88e3609568bd319
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921638

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