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Ethyl Acetate → (R)-5-(4-{1-ethyl-1-[4'-(1-hydroxy-1-methyl-ethyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxy)-4-hydroxy-pentanoic Acid

HRID 546826
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HRID 546826 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:21]([C:45]1[CH:58]=[CH:57][C:48]([O:49][CH2:50][C@@H:51]2[O:55][C:54](=[O:56])[CH2:53][CH2:52]2)=[C:47]([CH3:59])[CH:46]=1)([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([CH3:43])([O:38][Si](C)(C)C)[CH3:37])=[CH:32][CH:31]=2)=[C:26]([CH3:44])[CH:25]=1)[CH2:22][CH3:23])[CH3:20].C(OCC)(=[O:62])C>O1CCCC1>[CH2:19]([C:21]([C:45]1[CH:58]=[CH:57][C:48]([O:49][CH2:50][C@H:51]([OH:62])[CH2:52][CH2:53][C:54]([OH:55])=[O:56])=[C:47]([CH3:59])[CH:46]=1)([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([OH:38])([CH3:37])[CH3:43])=[CH:32][CH:31]=2)=[C:26]([CH3:44])[CH:25]=1)[CH2:22][CH3:23])[CH3:20]
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 57708923(R)-5-(4-{1-ethyl-1-[2-methyl-4'-(1-methyl-1-trimethylsilanyloxy-ethyl)-biphenyl-4-yl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one

생성물 1

HCID 57709071(R)-5-(4-{1-ethyl-1-[4'-(1-hydroxy-1-methyl-ethyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxy)-4-hydroxy-pentanoic Acid수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
75 °C

실험 절차

A 1.0 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.1 mL, 0.1 mmol) was added to a solution of (R)-5-(4-{1-ethyl-1-[2-methyl-4′-(1-methyl-1-trimethylsilanyloxy-ethyl)-biphenyl-4-yl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one (Example 15-(4); 16 mg, 0.028 mmol) in tetrahydrofuran (0.1 mL) at room temperature, and the mixture was stirred at 75° C. for two hours. Ethyl acetate was added to the reaction solution. The organic layer was washed with a potassium bisulfate aqueous solution and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane/methanol=10/1, developed three times) to give the title compound (11.3 mg, 78%).

후처리

  1. washThe organic layer was washed with a potassium bisulfate aqueous solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (dichloromethane/methanol=10/1, developed three times)

출처 및 근거

ORD 기록
ord-3f045fa57b0041059493c17c9e219f73
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935688B2

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