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Sodium potassium tartrate tetrahydrate → Progesterone Impurity D

HRID 1385618
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HRID 1385618 반응식
[C:1]([O:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:26])[CH2:17][CH2:18]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=[O:3])[CH3:2].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.CC(=O)CC.O>[C:1]([O:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 2724148Sodium potassium tartrate tetrahydrateHCID 21969303(3beta,20S)-pregn-5-ene-3,20-diol 20-acetate

생성물 1

HCID 57099835Progesterone Impurity D수율 82.2%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매
HCID 6569
Methyl Ethyl Ketone
용매

실험 절차

—Aluminium isopropoxide (18.1 g) was added to a solution of (3β,20S)-pregn-5-ene-3,20-diol 20-acetate (21.9 g) in dry toluene (252 ml) and dry 2-butanone (156 ml). The mixture was heated under reflux for 2 h, then cooled, whereupon a solution of potassium sodium tartrate tetrahydrate (91.4 g) in water (90 ml) was added. The mixture was stirred for 30 min. and filtered. The filtrate was poured into brine and the product extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography afforded (20S)-20-(acetyloxy)pregn-4-en-3-one (compound 6; 17.9 g).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. additionwas added
  4. filtrationfiltered
  5. additionThe filtrate was poured into brine
  6. extractionthe product extracted into ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5ec231da438b4998a4b701af36a73ae9
출처 데이터셋
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06262282B1

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