Hydrochloric Acid → 17alpha-Ethynyl-17beta-hydroxy-6,16-dimethyleneandrosta-4-en-3-one

HRID 370416

반응식

HRID 370416 반응식
[C:1]([C@:3]1([OH:34])[C:8](=[CH2:9])[CH2:7][C@H:6]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:4]12[CH3:5])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:23])[CH2:16][CH2:17]1)[C@H:12]([CH2:24]N(C1C=CC=CC=1)CC)[CH2:11]3)#[CH:2].Cl.O>C1COCC1>[C:1]([C@:3]1([OH:34])[C:8](=[CH2:9])[CH2:7][C@H:6]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:4]12[CH3:5])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:23])[CH2:16][CH2:17]1)[C:12](=[CH2:24])[CH2:11]3)#[CH:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 1331492617alpha-Ethynyl-17beta-hydroxy-6beta-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one

생성물 1

HCID 1331492917alpha-Ethynyl-17beta-hydroxy-6,16-dimethyleneandrosta-4-en-3-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

17α-Ethynyl-17β-hydroxy-6β-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one (Example 5) in THF (20 ml) are mixed. Degassed hydrochloric acid (6N, 55 ml plus 20 ml THF) are added. The mixture is stirred overnight at 20°-25° under nitrogen, at which time TLC shows the reaction to be complete. Water (110 ml) is added, the mixture filtered, the solids washed with 10% hydrochloric acid, twice with water, once with 5% sodium bicarbonate, and three times with water to neutrality. Solids were then dried under nitrogen overnight to give the title compound.

후처리

  1. customthe reaction
  2. filtrationthe mixture filtered
  3. washthe solids washed with 10% hydrochloric acid, twice with water, once with 5% sodium bicarbonate, and three times with water to neutrality
  4. customSolids were then dried under nitrogen overnight

출처 및 근거

ORD 기록
ord-4f9918abd77142c49503c4720ebaec35
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04526720

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