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2,3-Dihydroxybutanedioic Acid → 3-[5-(tert-Butyldimethylsilanyloxy)-5-(4-fluorophenyl)-1-(4-fluorophenylamino)-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)pentyl]benzonitrile

HRID 1612521
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HRID 1612521 반응식
C(N(C(C)C)CC)(C)C.[C:10]([Si:14]([CH3:42])([CH3:41])[O:15][CH:16]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[CH2:17][CH2:18][CH2:19][C:20]([N:22]1[CH:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][O:24][C:23]1=[O:33])=[O:21])([CH3:13])([CH3:12])[CH3:11].[F:43][C:44]1[CH:49]=[CH:48][C:47]([N:50]=[CH:51][C:52]2[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=2)[C:55]#[N:56])=[CH:46][CH:45]=1.C[Si](Cl)(C)C.C(O)(=O)C(C(C(O)=O)O)O.S([O-])(O)=O.[Na+]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[Si:14]([O:15][CH:16]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[CH2:17][CH2:18][CH:19]([C:20]([N:22]1[CH:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:25][O:24][C:23]1=[O:33])=[O:21])[CH:51]([C:52]1[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=1)[C:55]#[N:56])[NH:50][C:47]1[CH:46]=[CH:45][C:44]([F:43])=[CH:49][CH:48]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:42])[CH3:41]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 6

HCID 8752,3-Dihydroxybutanedioic AcidHCID 6397ChlorotrimethylsilaneHCID 81531DiisopropylethylamineHCID 121116183-[5-(tert-Butyldimethylsilanyloxy)-5-(4-fluorophenyl)pentanoyl]4-phenyloxazolidin-2-oneHCID 222520513-[(4-Fluorophenylimino)methyl]benzonitrileHCID 23665763Sodium Bisulfite

생성물 1

HCID 222520683-[5-(tert-Butyldimethylsilanyloxy)-5-(4-fluorophenyl)-1-(4-fluorophenylamino)-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)pentyl]benzonitrile

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

At 10° C., 24 ml of diisopropylethylamine are added to 14 g of 3-[5-(tert-butyidimethyl-silanyloxy)-5-(4-fluorophenyl)pentanoyl]-4-phenyloxazolidin-2-one (10) and 12.5 g of 3-[(4-fluorophenylimino)methyl]benzonitrile 11 in 200 ml of methylene chloride, and 7.1 ml of trimethylsilyl chloride are added dropwise. After 1 h, 3.4 ml of titanium tetrachloride are added dropwise at −10° C. The mixture is stirred at −10° C. for 3 h and then allowed to stand at −30° C. for another 12 h. 8 ml of acetic acid and 140 ml of a 7% strength aqueous tartaric acid solution are then added, and stirring is continued at room temperature for another 2 h. 50 ml of 20% strength aqueous sodium hydrogen sulfite solution are added, and the mixture is then stirred for another hour and extracted with methylene chloride. The organic phase is dried over magnesium sulfate, concentrated and purified by silica gel chromatography (ethyl acetate/heptane=1/3→1/1). This gives 12

후처리

  1. additionare added dropwise
  2. waitto stand at −30° C. for another 12 h
  3. stirringstirring
  4. waitis continued at room temperature for another 2 h
  5. stirringthe mixture is then stirred for another hour
  6. extractionextracted with methylene chloride
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (ethyl acetate/heptane=1/3→1/1)

출처 및 근거

ORD 기록
ord-9d45232736d44c60963e141a385cae44
출처 데이터셋
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06992067B2

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