Acetic Acid → {1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}-benzonitrile

HRID 1612516노트

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HRID 1612516 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:43])[CH2:9][CH2:10][CH:11]([C:29](N2C(C3C=CC=CC=3)COC2=O)=[O:30])[CH:12]([C:21]2[CH:28]=[CH:27][C:24](C#N)=[CH:23][CH:22]=2)[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.O.O.O.[F-].[CH2:48]([N+:52](CCCC)(CCCC)CCCC)CCC.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.C(O)(=O)C>C(OC)(C)(C)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:29](=[O:30])[CH:11]([CH2:10][CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[OH:43])[CH:12]2[C:21]2[CH:28]=[CH:27][CH:24]=[CH:23][C:22]=2[C:48]#[N:52])=[CH:15][CH:16]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 11708267BistrimethylsilylacetamidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 222520644-[5-(4-Fluorophenyl)-1-(4-fluorophenylamino)-5-hydroxy-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)-pentyl]-benzonitrile

생성물 1

HCID 22252073{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}-benzonitrile

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

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온도
40 °C

실험 절차

2 g of 5 are dissolved in 20 ml of methyl tert-butyl ether and, with 100 mg of tetrabutylammonium fluoride trihydrate and 1.3 ml of bistrimethylsilylacetamide, heated at 40° C. for about 1 h. The reaction is monitored by thin-layer chromatography. After the reaction has ended, initially 0.2 ml of glacial acetic acid is added, and the mixture is stirred for 30 min and concentrated. The residue is treated with 20 ml of a mixture of isopropanol/2N sulfuric acid=10:1 and stirred for 1 hour. Following the addition of a spatula tip of solid sodium bicarbonate, the mixture is once more concentrated under reduced pressure, the residue is taken up in ethyl acetate, the org. phase is washed with water and dried and the residue is, after removal of the solvent, purified by column chromatography (SiO2, CH2Cl2/methanol=100:1). This gives 6 of molecular weight 418.45 (C25H20F2N2O2); MS (DCl+): 419 (M+H+).

후처리

  1. concentrationconcentrated
  2. additionThe residue is treated with 20 ml of a mixture of isopropanol/2N sulfuric acid=10:1
  3. stirringstirred for 1 hour
  4. additionthe addition of a spatula tip of solid sodium bicarbonate
  5. concentrationthe mixture is once more concentrated under reduced pressure
  6. washphase is washed with water
  7. customdried
  8. customafter removal of the solvent
  9. custompurified by column chromatography (SiO2, CH2Cl2/methanol=100:1)
  10. customThis gives 6 of molecular weight 418.45 (C25H20F2N2O2)

출처 및 근거

ORD 기록
ord-c7c380d9874c41fcb21a18f76f859f34
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992067B2

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