Hydrochloric Acid → 3-[1-[4-(2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propionic acid

HRID 350326ノート

反応式

HRID 350326 の反応式
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:42]=[CH:41][C:17]([CH2:18][N:19]4[CH:23]=[C:22]([CH2:24][CH:25](C(OCC)=O)[C:26]([O:28]CC)=[O:27])[C:21]([C:36]5[S:37][CH:38]=[CH:39][CH:40]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C(O)C>[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:42]=[CH:41][C:17]([CH2:18][N:19]4[CH:23]=[C:22]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:21]([C:36]5[S:37][CH:38]=[CH:39][CH:40]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70124947diethyl [1-[4-(2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]methylmalonate

生成物 1

HCID 101409333-[1-[4-(2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propionic acid収率 85.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
110 °C

実験手順

A mixture of diethyl [1-[4-(2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]methylmalonate (1.75 g), 2N sodium hydroxide solution (10 ml), and ethanol (10 ml) was refluxed for 2 hour. After cooling, 1N hydrochloric acid (20 ml) was added to the mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless oily substance was dissolved in pyridine (30 ml), and stirred at 110° C. for 2 hours. After pyridine was removed under reduced pressure, ethyl acetate was added to the residue. The resulting solution was washed successively with dilute hydrochloric acid and saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless crystals were collected by filtration to obtain 3-[1-[4-(2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propionic acid (1.24 g, yield: 85%). This was recrystallized from ethyl acetate-hexane. Melting point: 145˜146° C.

後処理

  1. temperaturewas refluxed for 2 hour
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe resulting colorless oily substance was dissolved in pyridine (30 ml)
  8. customAfter pyridine was removed under reduced pressure, ethyl acetate
  9. additionwas added to the residue
  10. washThe resulting solution was washed successively with dilute hydrochloric acid and saturated aqueous sodium chloride solution
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated
  13. filtrationThe resulting colorless crystals were collected by filtration

出典と根拠

ORDレコード
ord-d3bcea634dc342cf9353c4422cfd70ef
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…