Hydrochloric Acid → 3-[1-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]-3-phenyl-1H-pyrazol-4-yl]propionic acid

HRID 350129ノート

反応式

HRID 350129 の反応式
[H-].[Na+].[C:3]1([C:9]2[C:13]([CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:22][C:23]1[CH:43]=[CH:42][C:26]([O:27][CH2:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:25][CH:24]=1.[OH-].[Na+].Cl>O1CCCC1.C(O)C.O.CN(C)C=O>[CH3:35][C:34]1[O:33][C:32]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[N:31][C:30]=1[CH2:29][CH2:28][O:27][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:11]2[CH:12]=[C:13]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[N:10]2)=[CH:43][CH:42]=1

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 118095944-[2-(4-Chloromethylphenoxy)ethyl]-5-methyl-2-phenyloxazoleHCID 178471160HCID 178471160、化合物

生成物 1

HCID 694226493-[1-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]-3-phenyl-1H-pyrazol-4-yl]propionic acid収率 71%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (60%, oily, 200 mg) was added to an N,N-dimethylformamide solution (15 ml) of ethyl 3-(3-phenyl-1H-pyrazole-4-yl)propionate (1.04 g) at 0° C., which was stirred at 0° C. for 30 minutes. 4-[2-(4-Chloromethylphenoxy)ethyl]-5-methyl-2-phenyloxazole (1.43 g) was added to the reaction mixture, which was stirred at room temperature overnight. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatography, and an oily substance was obtained from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). A mixture of the substance obtained, 1N aqueous sodium hydroxide solution (4 ml), ethanol (5 ml) and tetrahydrofuran (5 ml) was stirred for 2 hours at room temperature. The reaction mixture was acidified with dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The crystals obtained were collected by filtration to yield 3-[1-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]-3-phenyl-1H-pyrazol-4-yl]propionic acid (930 mg, yield: 71%). This was recrystallized from acetone-hexane. Melting point: 142–143° C.

後処理

  1. stirringwas stirred at room temperature overnight
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customan oily substance was obtained from the fraction
  7. washeluted with ethyl acetate-hexane (1:2, volume ratio)
  8. additionA mixture of the substance
  9. customobtained
  10. extractionwas extracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated
  14. customThe crystals obtained
  15. filtrationwere collected by filtration

出典と根拠

ORDレコード
ord-bb4535689a6a4eda96adb351577e9264
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

読み込み中…