Water → Deoxycholic Acid Impurity 69

HRID 1811520노트

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HRID 1811520 반응식
[Cl-].[Cl-].C([Al+2])C.[C:6]([O:10][CH3:11])(=[O:9])[CH:7]=[CH2:8].[C:12]([O:15][C@@H:16]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@H:18]([CH2:19][CH2:20][C@@H:21]3[C:31]2=[CH:30][CH2:29][C@@:28]2([CH3:36])[C@H:22]3[CH2:23][CH2:24]/[C:25]/2=[CH:26]/[CH3:27])[CH2:17]1)(=[O:14])[CH3:13].O>C(Cl)Cl>[C:12]([O:15][C@@H:16]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@H:18]([CH2:19][CH2:20][C@@H:21]3[C:31]2=[CH:30][CH2:29][C@@:28]2([CH3:36])[C@H:22]3[CH2:23][CH:24]=[C:25]2[C@H:26]([CH3:27])[CH2:8][CH2:7][C:6]([O:10][CH3:11])=[O:9])[CH2:17]1)(=[O:14])[CH3:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 16686341Ethyl aluminium dichlorideHCID 25145012(3R,5R,8S,10S,13S,14S,Z)-17-Ethylidene-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[A]phenanthren-3-YL acetate

생성물 1

HCID 25145010Deoxycholic Acid Impurity 69수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
25 °C

실험 절차

Ethyl aluminum dichloride (14.2 mL, 25 mmol, 1.8M in toluene) was added to a solution of methyl acrylate (1.89 mL, 20 mmol) in DCM (60 mL) at 0° C. under inert atmosphere. The resulting solution was stirred for 15 min and then compound 1.6a (3 g, 8.7 mmol) was added. After stifling for an additional 20 min at 0° C., the temperature was raised to 25° C. and held there for a further 18 h. At this point the reaction was determined to be complete by TLC, then the mixture was poured into cold (0° C.) water (60 mL). The phases were separated and the aqueous layer was extracted with DCM (60 mL). The organic layers were combined and washed sequentially with water (50 mL) and saturated brine solution (100 mL). It was then dried over anhydrous Na2SO4 (5 g) and filtered. The filtrate was concentrated under vacuum, providing compound 1.7b (2.6 g, 70%).

후처리

  1. waitAfter stifling for an additional 20 min at 0° C.
  2. waitheld there for a further 18 h
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with DCM (60 mL)
  5. washwashed sequentially with water (50 mL) and saturated brine solution (100 mL)
  6. dry with materialIt was then dried over anhydrous Na2SO4 (5 g)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-cbc8788f00754f91a73072ec43e3283e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362285B2

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