Potassium Carbonate → 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester

HRID 1643221ノート

反応式

HRID 1643221 の反応式
[CH2:1]([N:5]1[C:9]([CH2:10][NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:7]=[C:6]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:2][CH2:3][CH3:4].[O:33]([C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:40]Br)[C:34]([CH3:36])=[O:35].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:48]([O:47][C:45](=[O:46])[C:44]1[CH:43]=[CH:42][C:39]([CH2:40][N:11]([CH2:10][C:9]2[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:7][C:8]=2[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[CH:38][C:37]=1[O:33][C:34](=[O:35])[CH3:36])([CH3:51])([CH3:50])[CH3:49]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 184378533-Acetoxyl-4-tert-butoxycarbonyl-benzyl bromideHCID 58818024[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine

生成物 1

HCID 588179794-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester収率 63%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine (4.0 g, 9.31 mmol) and 3-acetoxyl-4-tert-butoxycarbonyl-benzyl bromide (3.37 g, 10.24 mmol, 1.1 eq.) in 50 ml anhydrous acetonitrile is added anhydrous potassium carbonate (2.82 g, 20.5 mmol, 2.2 eq.), the resulting mixture is stirred at room temperature for 1 h, then raised to 50° C., stirred overnight. The solid precipitate is filtered off, washed with ethyl acetate, the combined organics is concentrated to dryness, purified through silica gel flash chromatography to give 3.99 g of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester MS (+VE) m/z 680 (M+1).

後処理

  1. temperatureraised to 50° C.
  2. stirringstirred overnight
  3. filtrationThe solid precipitate is filtered off
  4. washwashed with ethyl acetate
  5. concentrationthe combined organics is concentrated to dryness
  6. custompurified through silica gel flash chromatography

出典と根拠

ORDレコード
ord-7b025043345248e5b2404c0d43cf4a37
出典データセット
uspto-grants-2012_02
特許番号
US08119665B2

反応ノート

読み込み中…