1-Chloro-4-(chloromethyl)benzene → 2-Butoxy-3-(4-{2-[1-(4-chloro-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid

HRID 1985158ノート

反応式

HRID 1985158 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.C([O:12][C:13](=[O:38])[C:14]([O:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH3:32])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH:25]2[CH2:29][NH:28][C:27](=[O:30])[N:26]2[CH3:31])=[CH:18][CH:17]=1)C.[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:34]([O:33][C:14]([CH3:32])([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH:25]2[CH2:29][N:28]([CH2:6][C:5]3[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:27](=[O:30])[N:26]2[CH3:31])=[CH:18][CH:17]=1)[C:13]([OH:38])=[O:12])[CH2:35][CH2:36][CH3:37]

参加物

6

反応物 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 688675082-Butoxy-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester

生成物 1

HCID 103113402-Butoxy-3-(4-{2-[1-(4-chloro-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Chlorobenzyl chloride (0.04 g, 0.174 mmol) and tetrabutyl ammonium iodide (catalytic amount) are added to a 0° C. suspension of 2-butoxy-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester (0.047 g, 0.116 mmol) and sodium hydride (0.012 g, 0.29 mmol, 60% suspension on mineral oil), pre-stirred for 1 h at ambient temperature. The reaction mixture is stirred at ambient temperature 48 h, diluted with ethyl acetate, and washed with 1N HCl and water. The organic layer is dried, concentrated, and purified by LCMS to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.27 (d, 2H, J=8.7 Hz), 7.17 (d, 2H, J=8.7 Hz), 7.07 (d, 2H, J=8.7 Hz), 7.71 (d, 2H, J=8.7 Hz), 4.34, 4.32 (ABq, 2H, J=15.0 Hz), 3.95 (t, 3H, J=5.9 Hz), 3.69-3.62 (m, 1H), 3.61-3.55 (m, 1H), 3.51-3.45 (m, 1H), 3.38 (t, 1H, J=8.7 Hz), 3.04-2.93 (m, 3H), 2.84 (s, 3H), 2.26-2.18 (m, 1H), 1.92-1.84 (m, 1H), 1.62-1.54 (m, 2H), 1.49 (s, 3H), 1.42-1.33 (m, 3H), 0.93 (t, 3H, J=7.3 Hz). MS [EI+] 503 (M+H)+, [EI−] 501 (M−H)+.

後処理

  1. stirringThe reaction mixture is stirred at ambient temperature 48 h
  2. washwashed with 1N HCl and water
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. custompurified by LCMS

出典と根拠

ORDレコード
ord-ed4b3d9733b5463d9abdcc08e347de4b
出典データセット
uspto-grants-2009_06
特許番号
US07544812B2

反応ノート

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