Diketene → HCID 178441547, compound

HRID 21861

Reaction equation

HRID 21861 reaction equation
[CH2:1]([C:5]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:8]2[CH:9]([C:13]([O:15][CH3:16])=[O:14])[NH:10][CH2:11][CH2:12][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:36]=[C:37]1[O:41][C:39](=[O:40])[CH2:38]1>CO>[CH2:1]([C:5]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:8]2[CH:9]([C:13]([O:15][CH3:16])=[O:14])[N:10]([C:39](=[O:40])[CH2:38][C:37]([CH3:36])=[O:41])[CH2:11][CH2:12][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 178441543HCID 178441543, compound

Product 1

HCID 178441547HCID 178441547, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of the compound obtained in Example 3 (0.50 g) and methanol (10 ml) is added diketene (0.20 g), and the mixture is stirred at room temperature for two hours. The mixture is evaporated under reduced pressure to remove the solvent, and to the residue is added chloroform. The mixture is washed, dried and evaporated under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate/methanol=10:10:1) to give methyl 2-n-butyl-5-acetoacetyl-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (0.29 g) as a foam.

Workup

  1. customThe mixture is evaporated under reduced pressure
  2. customto remove the solvent
  3. additionto the residue is added chloroform
  4. washThe mixture is washed
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate/methanol=10:10:1)

Sources & evidence

ORD record
ord-bccaab6738874d2abf60db28814d71ad
Source dataset
uspto-grants-1995_06
Patent number
US05424316

Linked notes

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