Methylamine → N-methyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxamide

HRID 52943

反応式

HRID 52943 の反応式
[CH3:1][NH2:2].[C:3]([O:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[C:27]([C:28](ON3C(=O)CCC3=O)=[O:29])=[C:26]([CH2:38][OH:39])[N:25]=[C:24]2[CH2:40][CH2:41][CH2:42][CH3:43])=[CH:18][CH:17]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O.C(Cl)Cl.CO>[CH3:1][NH:2][C:28]([C:27]1[N:23]([CH2:22][C:19]2[CH:18]=[CH:17][C:16]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:8]([O:7][C:3]([CH3:4])([CH3:5])[CH3:6])=[O:9])=[CH:21][CH:20]=2)[C:24]([CH2:40][CH2:41][CH2:42][CH3:43])=[N:25][C:26]=1[CH2:38][OH:39])=[O:29]

参加物

6

反応物 2

HCID 6329MethylamineHCID 19036239Succinimido 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate

生成物 1

HCID 19036316N-methyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxamide

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

0.4 ml of a 40% by volume solution of methylamine in water was added at room temperature to a solution of 0.278 g of succinimido 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate [prepared as described in Example 52(a)] in a mixture of 3 ml of methylene chloride and 2 ml of methanol, and the resulting mixture was allowed to stand for 16 hours at room temperature. At the end of this time, the solution was concentrated by evaporation under reduced pressure, and the concentrate was dissolved in ethyl acetate. The resulting solution was washed with an aqueous solution of potassium bisulfate and with an aqueous solution of sodium hydrogencarbonate, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 176 mg of the title compound as a glass.

後処理

  1. concentrationAt the end of this time, the solution was concentrated by evaporation under reduced pressure
  2. dissolutionthe concentrate was dissolved in ethyl acetate
  3. washThe resulting solution was washed with an aqueous solution of potassium bisulfate and with an aqueous solution of sodium hydrogencarbonate, in that order
  4. dry with materialafter which it was dried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through silica gel

出典と根拠

ORDレコード
ord-7c2def88fa374aaaa43921cb4adb7f74
出典データセット
uspto-grants-1997_04
特許番号
US05616599

関連ノート

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