Water → 4-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester

HRID 914360ノート

反応式

HRID 914360 の反応式
C(O[C:6](=[O:27])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][NH:18][C:19]2[N:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][N:20]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.[CH3:28][O:29][C:30](=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][CH:32]=1.[CH3:40][C:41]([CH3:44])([O-])[CH3:42].[K+].O>CN(C)C=O>[CH3:28][O:29][C:30](=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][N:18]([CH2:17][CH2:16][C:14]2[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([C:41]([CH3:44])([CH3:42])[CH3:40])=[O:27])[S:12][CH:13]=2)[C:19]2[N:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][N:24]=2)=[CH:33][CH:32]=1

参加物

6

反応物 4

HCID 962WaterHCID 256687Methyl 4-(bromomethyl)benzoateHCID 23665647Potassium tert-butoxideHCID 597588712-[(4-{2-[(5-Ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

生成物 1

HCID 673973504-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester収率 55.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-[(4-{2-[(5-Ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (3.0 g) synthesized in Example 265-1 and 4-(bromomethyl)benzoic acid methyl ester (2.0 g) were dissolved in N,N-dimethylformamide (37 mL), potassium tert-butoxide (0.91 g) was added thereto, and the mixture was stirred at room temperature for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1) to give the title compound (2.2 g) as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-aa6aea258a0e441f81eb3824768ab9a9
出典データセット
uspto-grants-2011_09
特許番号
US08026370B2

反応ノート

読み込み中…