Lithium Hydroxide → {8-Chloro-4-difluoromethoxy-3-[4-(2,2-dimethylpropionyl)benzyl]-2-ethylquinolin-5-yloxy}acetic acid

HRID 1922092ノート

反応式

HRID 1922092 の反応式
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:32][CH:33]([F:35])[F:34])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH2:17][CH3:18])[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26](=[O:31])[C:27]([CH3:30])([CH3:28])[CH3:29])=[CH:24][CH:25]=1)=[C:8]2[O:32][CH:33]([F:35])[F:34]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 67456452{8-Chloro-4-difluoromethoxy-3-[4-(2,2-dimethylpropionyl)benzyl]-2-ethylquinolin-5-yloxy}acetic acid methyl ester

生成物 1

HCID 25096076{8-Chloro-4-difluoromethoxy-3-[4-(2,2-dimethylpropionyl)benzyl]-2-ethylquinolin-5-yloxy}acetic acid収率 57.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of {8-chloro-4-difluoromethoxy-3-[4-(2,2-dimethylpropionyl)benzyl]-2-ethylquinolin-5-yloxy}acetic acid methyl ester (0.071 g) in tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.28 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated to low bulk under reduced pressure, acidified by the addition of 0.1 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and then concentrated under reduced pressure. Purification of the residue by preparative reverse-phase HPLC gave title compound as a yellow solid (0.040 g).

後処理

  1. concentrationThe mixture was concentrated to low bulk under reduced pressure
  2. additionacidified by the addition of 0.1 M aqueous hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by preparative reverse-phase HPLC

出典と根拠

ORDレコード
ord-4a14c83d668b4052956bd2a0131654d5
出典データセット
uspto-grants-2012_05
特許番号
US08173812B2

反応ノート

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