6-{4-[3-(2,5-Dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonate → 3-(3-{4-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione

HRID 857096ノート

反応式

HRID 857096 の反応式
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[C:27](=[O:28])[CH2:26][NH:25][C:24]2=[O:29])[CH:18]=1)(=O)=O.[NH2:30][CH2:31][C@@H:32]([C:34]1[CH:45]=[CH:44][C:37]2[O:38][C:39]([CH3:43])([CH3:42])[O:40][CH2:41][C:36]=2[CH:35]=1)[OH:33]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:42][C:39]1([CH3:43])[O:38][C:37]2[CH:44]=[CH:45][C:34]([C@@H:32]([OH:33])[CH2:31][NH:30][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([N:23]4[C:27](=[O:28])[CH2:26][NH:25][C:24]4=[O:29])[CH:20]=[CH:21][CH:22]=3)=[CH:35][C:36]=2[CH2:41][O:40]1

参加物

5

反応物 2

HCID 218672176-{4-[3-(2,5-Dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonateHCID 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanol

生成物 1

HCID 693439983-(3-{4-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione収率 41.9%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

A solution of 6-{4-[3-(2,5-dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonate (766 mg) in DMF (8 ml) was treated with tetrabutylammonium bromide (578 mg) and (1R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (544 mg) and the mixture was stirred at 20° C. for 3 d. The solvent was removed under reduced pressure, the residue was dissolved in CH2Cl2, washed with water and purified by chromatography on Biotage (40 g) eluting with 3% 2M NH3 in MeOH:CH2Cl2 to give the title compound (417 mg). ES+ve 554 (MH)+.

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. custompurified by chromatography on Biotage (40 g)
  5. washeluting with 3% 2M NH3 in MeOH

出典と根拠

ORDレコード
ord-fa08fb941b7f408493cdbe8dc12f1042
出典データセット
uspto-grants-2006_12
特許番号
US07144908B2

反応ノート

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