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

HRID 133725

반응식

HRID 133725 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>COC(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 4-[5-(4-Fluorophenyl)-1-(4-fluorophenylamino)-5-hydroxy-2-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-pentyl]-benzonitrile were dissolved in 20 ml of methyl-tert-butyl ether and, together with 100 mg of tetrabutylammonium fluoride trihydrate and 1.3 ml of bistrimethylsilyl acetamide, heated at 40° C. for about 1 h. The reaction was monitored by thin-layer chromatography. After the reaction ended, 0.2 ml of glacial acetic acid were initially added and the mixture was stirred for 30 min and then concentrated. 20 ml of a mixture of isopropanol/2N sulfuric acid=10:1 were added to the residue, and the mixture was stirred for 1 hour. Following addition of a spatula tip of solid sodium bicarbonate, the mixture was again concentrated under reduced pressure. The residue was taken up in ethyl acetate and the organic phase was washed with water and dried. The residue was, after removal of the solvent, purified by column chromatography (SiO2, CH2Cl2/methanol=100:1). This gave the product of molecular weight 418.45 (C25H20F2N2O2); MS (DCI+) 419 (M+H+).

후처리

  1. concentrationconcentrated
  2. addition20 ml of a mixture of isopropanol/2N sulfuric acid=10:1 were added to the residue
  3. stirringthe mixture was stirred for 1 hour
  4. additionaddition of a spatula tip of solid sodium bicarbonate
  5. concentrationthe mixture was again concentrated under reduced pressure
  6. washthe organic phase was washed with water
  7. customdried
  8. customafter removal of the solvent
  9. custompurified by column chromatography (SiO2, CH2Cl2/methanol=100:1)
  10. customThis gave the product of molecular weight 418.45 (C25H20F2N2O2)

출처 및 근거

ORD 기록
ord-4ed0447e78444586b58761d51af3f404
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390790B2

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