Potassium Iodide → (S)-2-Ethoxy-3-[2-methyl-4-(5-methyl-2-o-tolyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid methyl ester

HRID 1064881노트

반응식

HRID 1064881 반응식
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([O:14][CH2:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].Cl[CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[O:23][C:24]=1[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([O:14][CH2:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[O:23][C:24]=2[CH3:25])=[CH:8][C:7]=1[CH3:13]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 219742584-(Chloromethyl)-5-methyl-2-(2-methylphenyl)-1,3-oxazoleHCID 68616579(S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester

생성물 1

HCID 69280462(S)-2-Ethoxy-3-[2-methyl-4-(5-methyl-2-o-tolyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid methyl ester수율 70.6%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of (S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (80 mg, 0.34 mmol), 4-chloromethyl-5-methyl-2-o-tolyl-oxazole (82 mg, 0.37 mmol), cesium carbonate (120 mg, 0.37 mmol) and a trace of potassium iodide were suspended in acetone (8 ml). The suspension was heated under reflux for 5 h, the solvent evaporated under reduced pressure and the residue dissolved in 2 N HCl/ice water 1/1 and ethyl acetate. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed two times with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, cyclohexane/AcOEt) to give 100 mg (0.24 mmol, 70%) of the title compound as yellow oil.

후처리

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 5 h
  3. customthe solvent evaporated under reduced pressure
  4. dissolutionthe residue dissolved in 2 N HCl/ice water 1/1
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted two times with ethyl acetate
  7. washThe combined organic layers were washed two times with brine
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe residue purified by column chromatography (silica gel, cyclohexane/AcOEt)

출처 및 근거

ORD 기록
ord-3dbcf44e59ee4ff99c88759e84e6073e
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969725B2

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