Ammonium Acetate → Ethyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylate

HRID 733734Notes

Reaction equation

HRID 733734 reaction equation
[CH2:1]([O:3][C:4]([C:6]([C:9]1[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:11]=[CH:12][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]O)=[O:5])[CH3:2].C([O-])(=O)C.[NH4+:32]>C(O)C>[NH2:32][CH:7]=[C:6]([C:9]1[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:11]=[CH:12][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 68867283Ethyl 2-{1-[(ethyloxy)carbonyl]-2-hydroxyethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylate

Product 1

HCID 68866632Ethyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylateYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-{1-[(ethyloxy)carbonyl]-2-hydroxyethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylate (6.59 g), ammonium acetate (6.47 g) and ethanol (80 ml) was stirred at 60° C. under argon for 4 h, at room temperature over night then heated at 60° C. for a further hour. After cooling the solvent was evaporated and the residue partitioned between ethyl acetate and water, extracting the separated aqueous layer three times with ethyl acetate. The combined organic layers were washed with brine then dried (MgSO4), filtered and evaporated. The residue was stirred in n-hexane for 1 h and then the mixture was allowed to settle. The n-hexane was decanted off and the oil dried to afford the title compound as a brown oil (4.99 g).

Workup

  1. temperaturethen heated at 60° C. for a further hour
  2. temperatureAfter cooling the solvent
  3. customwas evaporated
  4. customthe residue partitioned between ethyl acetate and water
  5. extractionextracting the separated aqueous layer three times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialthen dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. stirringThe residue was stirred in n-hexane for 1 h
  11. customThe n-hexane was decanted off
  12. customthe oil dried

Sources & evidence

ORD record
ord-ad67a0c1f4064973b4fcb9c6703538bc
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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