Acetic Acid → 5beta-Chol-9(11)-en-24-oic acid, 3alpha-hydroxy-12-oxo-, methyl ester, acetate

HRID 1671722노트

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HRID 1671722 반응식
[C:1]([O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C:26]2=[CH:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)(=[O:3])[CH3:2].CC(O)=[O:34]>>[C:1]([O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C:26]2=[CH:25][C:24](=[O:34])[C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)(=[O:3])[CH3:2]

참가 물질

3

반응물 2

HCID 176Acetic AcidHCID 59365567(R)-Methyl 4-((3R,5R,8S,10S,13R,14S,17R)-3-acetoxy-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

생성물 1

HCID 2400245beta-Chol-9(11)-en-24-oic acid, 3alpha-hydroxy-12-oxo-, methyl ester, acetate수율 50%

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온도
50 °C

실험 절차

CrO3 (17.0 g, 170 mmol) was added to a solution of compound 1.8a (17 g, 39.5 mmol) in AcOH (270 mL). The resulting mixture was heated at 50° C. for 24-36 h. Upon complete disappearance of the starting material by TLC, the solvent was evaporated under vacuum and the crude material was dissolved in ethyl acetate (400 mL) and water (200 mL). The two phases were separated and the organic layer was washed twice with water (2×100 mL) and then once with saturated brine solution (100 mL). The organic phase was dried over anhydrous Na2SO4 (40 g) and filtered. The filtrate was concentrated under vacuum and the resulting solid was purified by column chromatography [49 mm (W)×600 mm (L), 60-120 mesh silica, 120 g], eluting with ethyl acetate/hexane (1:5) [10 mL fractions, 3 mL/min elution, monitored by TLC and detected with UV light (254 nm) lamp]. The product-containing fractions were combined and concentrated under vacuum to afford compound 1.9a (8.8 g, 50% yield) as a white solid.

후처리

  1. customUpon complete disappearance of the starting material by TLC, the solvent was evaporated under vacuum
  2. dissolutionthe crude material was dissolved in ethyl acetate (400 mL)
  3. customThe two phases were separated
  4. washthe organic layer was washed twice with water (2×100 mL)
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4 (40 g)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum
  8. customthe resulting solid was purified by column chromatography [49 mm (W)×600 mm (L), 60-120 mesh silica, 120 g]
  9. washeluting with ethyl acetate/hexane (1:5) [10 mL fractions, 3 mL/min elution, monitored by TLC and detected with UV light (254 nm) lamp]
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-d081a86217bb499a8659e713647d6161
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994351B2

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