Sodium hydride → Rac-2-ethoxy-3-[2-methyl-1-(2-phenyl-thiazol-4-ylmethyl)-1h-indol-5-yl]-propionic acid

HRID 2181236노트

반응식

HRID 2181236 반응식
C([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:16])=[CH:10]2)C.Cl[CH2:22][C:23]1[N:24]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:26][CH:27]=1.[H-].[Na+]>CN(C)C=O.O>[CH2:18]([O:17][CH:5]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:22][C:23]1[N:24]=[C:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[S:26][CH:27]=1)[C:11]([CH3:16])=[CH:10]2)[C:4]([OH:3])=[O:20])[CH3:19]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleHCID 69563210HCID 69563210, 화합물

생성물 1

HCID 9979540Rac-2-ethoxy-3-[2-methyl-1-(2-phenyl-thiazol-4-ylmethyl)-1h-indol-5-yl]-propionic acid수율 90.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

0.28 g (1.0 mmol) rac-2-ethoxy-3-(2-methyl-1H-indol-5-yl)-propionic acid ethyl ester (preparation 5) were reacted with 0.23 g (1.1 mmol) 4-chloromethyl-2-phenyl-thiazole in 5 ml N,N-dimethylformamide in the presence of 0.09 g (2.0 mmol) sodium hydride (55%) in mineral oil) at room temperature for 16 hours. The reaction mixture was then diluted with water and extracted with dichloromethane. The combined organic phases were dried over MgSO4 and evaporated. The residue formed was purified by flash-chromatography (silica gel; eluent: gradient of n-heptane and ethyl acetate) to give 0.38 g (90%) of rac-2-ethoxy-3-[2-methyl-1-(2-phenyl-thiazol-4-ylmethyl)-1H-indol-5-yl]-propionic acid as light brown solid.

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customevaporated
  4. customThe residue formed
  5. customwas purified by flash-chromatography (silica gel; eluent: gradient of n-heptane and ethyl acetate)

출처 및 근거

ORD 기록
ord-68cb26092b95480481da26761dd226be
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06890947B2

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