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Potassium Carbonate → n-(4-Oxazol-5-yl-phenyl)-2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionamide

HRID 1393913
ノート
印刷プレビュー

反応式

HRID 1393913 の反応式
S(Cl)(Cl)=O.[O:5]=[C:6]([CH2:10][C:11]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])[CH2:14][CH2:13][CH2:12]1)[C:7]([OH:9])=O.[O:25]1[C:29]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)=[CH:28][N:27]=[CH:26]1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[O:25]1[C:29]([C:30]2[CH:31]=[CH:32][C:33]([NH:36][C:7](=[O:9])[C:6](=[O:5])[CH2:10][C:11]3([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:21]([F:22])([F:23])[F:24])[CH2:14][CH2:13][CH2:12]3)=[CH:34][CH:35]=2)=[CH:28][N:27]=[CH:26]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 5177474-(1,3-Oxazol-5-yl)anilineHCID 596809512-Oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionic acid

生成物 1

HCID 16738962n-(4-Oxazol-5-yl-phenyl)-2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionamide収率 42.1%

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
-5 °C

実験手順

0.052 ml of thionyl chloride was added to a solution of 0.1 g of 2-Oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionic acid in 2 ml of dimethyl acetamide at −5° C., and stirred for 30 min at −5° C. Then 56 mg of 4-oxazol-5-yl-phenylamine was added in solid form and stirred for 1 hour at room temperature. Potassium carbonate was added and stirred overnight at room temperature. The reaction was quenched with water and extracted with ethyl acetate. The combined ethyl acetate extracts were washed twice with water, dried and concentrated by evaporation. The residue was purified by column chromatography on silica-gel (EtOAc-hexane 10%-20%) to yield 63 mg of product.

後処理

  1. stirringstirred for 1 hour at room temperature
  2. stirringstirred overnight at room temperature
  3. customThe reaction was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate extracts were washed twice with water
  6. customdried
  7. concentrationconcentrated by evaporation
  8. customThe residue was purified by column chromatography on silica-gel (EtOAc-hexane 10%-20%)

出典と根拠

ORDレコード
ord-4a056b89f30c41108fa62d640dfa783d
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07348322B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート