Triethylamine → 8-Amino-8-(benzoylhydrazono)octanoic acid ethyl ester

HRID 1039169Notes

Reaction equation

HRID 1039169 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](OCC)=[NH:19])[CH3:9].[C:24]([NH:32][NH2:33])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:8]([O:10][C:11](=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH2:19])=[N:33][NH:32][C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11955BenzoylhydrazineHCID 860347247-Ethoxycarbonimidoylheptanoic acid ethyl ester

Product 1

HCID 684915428-Amino-8-(benzoylhydrazono)octanoic acid ethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add triethylamine (5.6 mL, 40 mmol) to a solution of 7-ethoxycarbonimidoylheptanoic acid ethyl ester (11.0 g, 41 mmol) and benzoic acid hydrazide (5.5 g, 40 mmol) in ethanol (110 mL) at room temperature under nitrogen and stir the mixture for 12 hours. Remove the solvent under reduced pressure, dissolve the residue in ethyl acetate (200 mL), wash with saturated NaHCO3 (200 mL) and brine (200 mL) solutions, and dry over sodium sulfate. Remove the solvent under reduced pressure to provide 8-amino-8-(benzoylhydrazono)octanoic acid ethyl ester (8.3 g, 64%).

Workup

  1. customRemove the solvent under reduced pressure
  2. dissolutiondissolve the residue in ethyl acetate (200 mL)
  3. washwash with saturated NaHCO3 (200 mL) and brine (200 mL) solutions
  4. dry with materialdry over sodium sulfate
  5. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-d4f0a25e6159435f9a5ff52e4b0c8319
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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