Cesium carbonate → 2-Methyl-3-(3-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

HRID 1985205노트

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HRID 1985205 반응식
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[CH3:2].[CH3:23][N:24]1[CH:28]([CH2:29][CH2:30]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:27][N:26]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=2)[C:25]1=[O:53].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:30][CH2:29][CH:28]2[CH2:27][N:26]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([C:49]([F:51])([F:52])[F:50])=[CH:45][CH:44]=3)[C:25](=[O:53])[N:24]2[CH3:23])[CH:8]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 688673493-(3-Hydroxy-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl esterHCID 86596229HCID 86596229, 화합물

생성물 1

HCID 688674542-Methyl-3-(3-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
55 °C

실험 절차

To a solution of 3-(3-Hydroxy-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (Isomer 2) (43 mg, 0.143 mmol,) and Toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (Isomer 2) (72 mg, 0.157 mmol) in DMF (1 ml) at 23° C. is added Cs2CO3 (61 mg, 0.186 mmol) and the suspension heated at 55° C. for 7 hours. The mixture is cooled, filtered, and the filter cake washed with DMF (10 ml). The filtrate is poured into 1N HCl (35 ml) and extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water (25 ml), brine (20 ml), dried (Na2SO4) and concentrated to an oil. Purification by flash chromatography on a Biotage silica cartridge (gradient elution, 4:1 hexanes:acetone to 1:1 hexanes:acetone) provided an oil, (72 mg, 87%) (diastereomer 4).

후처리

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. washthe filter cake washed with DMF (10 ml)
  4. additionThe filtrate is poured into 1N HCl (35 ml)
  5. extractionextracted with ethyl acetate (2×20 ml)
  6. washThe combined organic extracts were washed with water (25 ml), brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to an oil
  9. customPurification by flash chromatography
  10. washon a Biotage silica cartridge (gradient elution, 4:1 hexanes:acetone to 1:1 hexanes:acetone)
  11. customprovided an oil, (72 mg, 87%) (diastereomer 4)

출처 및 근거

ORD 기록
ord-480e991a3f2645d099803e37da763e12
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544812B2

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