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

HRID 52943
Notes
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Reaction equation

HRID 52943 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7c2def88fa374aaaa43921cb4adb7f74
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05616599

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes