Methyl 4-chloroformylbutyrate → 4-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylcarbamoyl]-butyric acid methyl ester

HRID 1093007

反応式

HRID 1093007 の反応式
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[F:11][C:12]1[CH:13]=[C:14]([C:22]2[S:26][C:25]([NH2:27])=[N:24][C:23]=2[CH3:28])[CH:15]=[CH:16][C:17]=1[S:18]([CH3:21])(=[O:20])=[O:19]>>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:27][C:25]1[S:26][C:22]([C:14]2[CH:15]=[CH:16][C:17]([S:18]([CH3:21])(=[O:19])=[O:20])=[C:12]([F:11])[CH:13]=2)=[C:23]([CH3:28])[N:24]=1

参加物

3

反応物 2

HCID 73916Methyl 4-chloroformylbutyrateHCID 573512775-(3-Fluoro-4-(methylsulfonyl)phenyl)-4-methylthiazol-2-amine

生成物 1

HCID 866407654-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylcarbamoyl]-butyric acid methyl ester

反応条件

温度
60 °C

実験手順

Methyl-4-(chloroformyl)butyrate (4.0 mmol) is added to a stirred solution of 5-(3-fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Example 72) (0.77 g, 2.69 mmol) and heated to 60° C. for 1.5 hours. The reaction mixture is allowed to cool to room temperature and the solvent removed in vacuo. The residue is washed with saturated sodium bicarbonate solution (2×50 ml) and water (1×50 ml). The product is extracted with ethyl acetate (2×50 ml) and the combined organic extracts dried (MgSO4). Removal of the solvent followed by recrystallisation from ethyl acetate affords the titled compound.

後処理

  1. temperatureto cool to room temperature
  2. customthe solvent removed in vacuo
  3. washThe residue is washed with saturated sodium bicarbonate solution (2×50 ml) and water (1×50 ml)
  4. extractionThe product is extracted with ethyl acetate (2×50 ml)
  5. dry with materialthe combined organic extracts dried (MgSO4)
  6. customRemoval of the solvent
  7. customfollowed by recrystallisation from ethyl acetate

出典と根拠

ORDレコード
ord-ae1dfa604db74780b088a52302463771
出典データセット
uspto-grants-2012_03
特許番号
US08129541B2

関連ノート

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