Cesium carbonate → 3-(2-Oxooxazolidin-3-yl)benzoic Acid Methyl Ester

HRID 1612441노트

반응식

HRID 1612441 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[O:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([N:20]2[CH2:21][CH2:22][O:18][C:19]2=[O:23])[CH:3]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 12070Methyl 3-bromobenzoateHCID 739492-OxazolidinoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

생성물 1

HCID 695897133-(2-Oxooxazolidin-3-yl)benzoic Acid Methyl Ester수율 21.9%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

Methyl 3-bromobenzoate (500 mg, 2.33 mmol), caesium carbonate (1.06 g, 3.26 mmol), oxazolidin-2-one (243 mg, 2.80 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (107 mg, 0.186 mmol) and tris(dibenzylideneacetone)dipalladium (0) (43 mg, 0.047 mmol) were refluxed under argon in dioxane (6 ml) for 18 h. After cooling, the mixture was filtered and evaporated in vacuo. Column chromatography on silica gel eluting with a gradient of 10–50% ethyl acetate in hexane gave the title compound (113 mg).

후처리

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-5fc2000416bf4e678773e8b3eb663a12
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992103B2

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