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

HRID 52943

반응식

HRID 52943 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7c2def88fa374aaaa43921cb4adb7f74
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616599

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