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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Benzoyl chloride → 1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl) 2,2-dimethylsuccinate

HRID 513903
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인쇄 미리보기

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HRID 513903 반응식
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([CH:28]=[O:29])[CH2:23][C:22](=[O:24])[C:21]([CH:25]([CH3:27])[CH3:26])=[C:12]32)[C:3]1([CH3:33])[CH3:32].[C:34]([O:38][C:39](=[O:47])[C:40]([CH3:46])([CH3:45])[CH2:41][C:42](O)=[O:43])([CH3:37])([CH3:36])[CH3:35].C(Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.O.C(OCC)(=O)C.C1COCC1>[CH3:45][C:40]([CH3:46])([CH2:41][C:42]([O:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([CH:28]=[O:29])[CH2:23][C:22](=[O:24])[C:21]([CH:25]([CH3:27])[CH3:26])=[C:12]32)[C:3]1([CH3:32])[CH3:33])=[O:43])[C:39]([O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:47]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 235551774-(Tert-butoxy)-3,3-dimethyl-4-oxobutanoic acidHCID 86690401(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-Hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysene-3a-carbaldehyde

생성물 1

HCID 86690400
1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl) 2,2-dimethylsuccinate

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-Hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysene-3a-carbaldehyde (26.9 g, 1 equiv), 4-(tert-butoxy)-3,3-dimethyl-4-oxobutanoic acid (14.96 g, 1.25 equiv) and THF (538 ml, 20 vol) were charged to a flask. Benzoyl chloride (10.4 g, 1.25 equiv) was added followed by slow addition of triethylamine (14.97 g, 2.5 equiv) forming a thick slurry. DMAP (0.1.81 g, 0.25 equiv) was added and the reaction was allowed to stir at ambient temperature for approximately 18 hours until complete by HPLC. Reaction was then charged with ethyl acetate (538 mL, 20 vol) and water (269 ml, 10 vol), stirred well and allowed to settle. Aqueous phase was removed and the organic phase washed with saturated sodium bicarbonate solution (2×10 vol) followed by water (269 mL, 10 vol). The reaction solution evaporated under vacuum to approximately 4 volumes to produce solids. Additional hexanes (269 ml, 10 vol) was added and reaction heated back to reflux to nearly form solution and slowly cooled to ambient temperature (seeding with desired product) and let stir for 15 minutes then cooled to 0° C. for approximately two hours and filtered solid. Washed solid with hexanes (2×10 vol) and dried at 50° C. under vacuum to a weight of 32.15 g, 85% yield of 1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl) 2,2-dimethylsuccinate.

후처리

  1. customforming a thick slurry
  2. customReaction
  3. stirringstirred well
  4. customAqueous phase was removed
  5. washthe organic phase washed with saturated sodium bicarbonate solution (2×10 vol)
  6. customThe reaction solution evaporated under vacuum to approximately 4 volumes
  7. customto produce solids
  8. customreaction
  9. temperatureheated back
  10. temperatureto reflux
  11. customto nearly form solution

출처 및 근거

ORD 기록
ord-1e9fd932e27242738b3f0409af9286ab
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102685B2

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