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

HRID 1093007

반응식

HRID 1093007 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ae1dfa604db74780b088a52302463771
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129541B2

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