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 1985158노트

반응식

HRID 1985158 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ed4b3d9733b5463d9abdcc08e347de4b
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544812B2

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