Oxalyl chloride → Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

HRID 52965ノート

反応式

HRID 52965 の反応式
C(Cl)(=O)C(Cl)=O.C([NH:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:30]([C:37]([OH:40])([CH3:39])[CH3:38])[N:29]=[C:28]2[CH2:41][CH2:42][CH3:43])=[CH:22][CH:21]=1)=O)(C)(C)C>C(Cl)Cl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:30]([C:37]([OH:40])([CH3:38])[CH3:39])[N:29]=[C:28]2[CH2:41][CH2:42][CH3:43])=[CH:22][CH:21]=1)#[N:11]

参加物

6

反応物 2

HCID 65578Oxalyl chlorideHCID 19036152Ethyl 1-{4-[2-(t-butylaminocarbonyl)phenyl]phenyl}methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

生成物 1

HCID 15461993Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate収率 80.9%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

0.345 ml of oxalyl chloride was added dropwise, whilst ice-cooling, to a solution of 1.00 g of ethyl 1-{4-[2-(t-butylaminocarbonyl)phenyl]phenyl}methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate [prepared as described in step (a) above] in 10 ml of methylene chloride, and the mixture was stirred at the same temperature for 2 hours. At the end of this time, the reaction mixture was diluted with an aqueous solution of sodium hydrogencarbonate and ethyl acetate, and the ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 0.69 g of the title compound as crystals.

後処理

  1. customthe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

出典と根拠

ORDレコード
ord-c26bfc275e1c48588343a28324306729
出典データセット
uspto-grants-1997_04
特許番号
US05616599

反応ノート

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