Triethylamine → Ethyl [(5-methoxy-2-nitrobenzyl)-(4-chlorobenzoyl)amino]acetate

HRID 2417522Notes

Reaction equation

HRID 2417522 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8](O)=O.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].CS(Cl)(=O)=O.Cl.[CH2:36]([O:38][C:39](=[O:42])[CH2:40][NH2:41])[CH3:37].C(=O)([O-])O.[Na+].[Cl:48][C:49]1[CH:57]=[CH:56][C:52]([C:53](Cl)=[O:54])=[CH:51][CH:50]=1>C1COCC1.ClCCl.C(O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[CH2:8][N:41]([CH2:40][C:39]([O:38][CH2:36][CH3:37])=[O:42])[C:53](=[O:54])[C:52]1[CH:56]=[CH:57][C:49]([Cl:48])=[CH:50][CH:51]=1

Participants

13

Reactant 8

HCID 8471Triethylamine3×HCID 85014-Chlorobenzoyl chlorideHCID 10928Ethyl chloroformateHCID 31297Methanesulfonyl chlorideHCID 3392095-Methoxy-2-nitrobenzoic acidHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 86589884Ethyl [(5-methoxy-2-nitrobenzyl)-(4-chlorobenzoyl)amino]acetate

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent4×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.0 g (15.2 mmol) of 5-methoxy-2-nitrobenzoic acid was dissolved in a mixture of 200 ml of THF and 2.7 ml (19.8 mmol) of triethylamine. 1.7 ml (17.6 mmol) of ethyl chloroformate was added to the obtained solution under cooling with ice, and they were stirred for 15 minutes. A piece of ice was added to the obtained filtrate, and then 1.1 g (30.4 mmol) of sodium borohydride was added thereto under cooling with ice. The temperature was elevated to room temperature, and the obtained mixture was stirred overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 100 ml of dichloromethane. 1.4 ml (18.2 mmol) of methanesulfonyl chloride and 3.2 ml (22.8 mmol) of triethylamine were added to the obtained solution, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 100 ml of ethanol. 3.2 g (22.8 mmol) of glycine ethyl ester hydrochloride and 2.6 g (30.4 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. for 6 hours. The solvent was evaporated. After the extraction with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 70 ml of dichloromethane. 0.63 ml (4.9 mmol) of 4-chlorobenzoyl chloride and 0.86 ml (6.2 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. additionA piece of ice was added to the obtained filtrate
  3. temperatureunder cooling with ice
  4. customwas elevated to room temperature
  5. stirringthe obtained mixture was stirred overnight
  6. stirringwere stirred
  7. temperatureunder cooling with ice for 2 hours
  8. stirringwere stirred at 70° C. for 6 hours
  9. customThe solvent was evaporated
  10. extractionAfter the extraction with ethyl acetate as the extracting solvent by an ordinary method
  11. customthe obtained crude product
  12. temperatureunder cooling with ice, and they
  13. stirringwere stirred
  14. temperatureunder cooling with ice for 2 hours
  15. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-ef98afa6537a4dc29aa857fac681e694
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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