Potassium Carbonate → 2-(4-Fluoro-3-methyl-phenylamino)-hexanoic acid methyl ester

HRID 885500ノート

反応式

HRID 885500 の反応式
[CH3:1][O:2][C:3](=[O:10])[CH:4](Br)[CH2:5][CH2:6][CH2:7][CH3:8].[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=1[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:10])[CH:4]([NH:16][C:15]1[CH:17]=[CH:18][C:12]([F:11])=[C:13]([CH3:19])[CH:14]=1)[CH2:5][CH2:6][CH2:7][CH3:8]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 679814-Fluoro-m-toluidineHCID 95578Hexanoic acid, 2-bromo-, methyl ester

生成物 1

HCID 691697822-(4-Fluoro-3-methyl-phenylamino)-hexanoic acid methyl ester収率 45%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-bromo-hexanoic acid methyl ester (0.500 g, 2.404 mmol) and 4-fluoro-3-methylaniline (0.301 g, 2.404 mmol) in 15 mL of DMF, was added K2CO3 (1.661 g, 12.020 mmol). After stirring at room temperature under N2 for 88 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined dried over anhydrous Na2SO4 and the solvent removed under reduced pressure. Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes afforded the title compound as brown oil (0.273 g, 45% yield). LC-MS: tR=9.9 min; m/z 254 (M+H)+.

後処理

  1. extractionextracted with dichloromethane (60 mL×3)
  2. dry with materialThe organic extracts were combined dried over anhydrous Na2SO4
  3. customthe solvent removed under reduced pressure
  4. washFlash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-e2915520c606496aaa3ffa9e9ad42f01
出典データセット
uspto-grants-2012_08
特許番号
US08242174B2

反応ノート

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