Triethylamine → HCID 86589886, compound

HRID 2417525Notes

Reaction equation

HRID 2417525 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[BH4-].[Na+].CS(Cl)(=O)=O.C(N(CC)CC)C.Cl.[CH2:29]([O:31][C:32](=[O:35])[CH2:33][NH2:34])[CH3:30].C(=O)([O-])O.[Na+].[Cl:41][C:42]1[CH:50]=[CH:49][C:45]([C:46](Cl)=[O:47])=[CH:44][CH:43]=1>C(O)C.C1COCC1.ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][N:34]([CH2:33][C:32]([O:31][CH2:29][CH3:30])=[O:35])[C:46](=[O:47])[C:45]1[CH:49]=[CH:50][C:42]([Cl:41])=[CH:43][CH:44]=1

Participants

12

Reactant 7

HCID 8471Triethylamine2×HCID 85014-Chlorobenzoyl chlorideHCID 31297Methanesulfonyl chlorideHCID 988673-Methoxy-2-nitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 86589886HCID 86589886, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent4×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.5 g (13.8 mmol) of 3-methoxy-2-nitrobenzaldehyde was dissolved in a mixture of 70 ml of ethanol and 70 ml of THF. 1.0 g (27.6 mmol) of sodium borohydride was added to the obtained solution. They were stirred at room temperature 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. 1.3 ml (16.6 mmol) of methanesulfonyl chloride and 2.9 ml (20.7 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 70 ml of ethanol. 2.9 g (20.7 mmol) of glycine ethyl ester hydrochloride and 2.3 g (27.6 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 100 ml of dichloromethane. 2.0 ml (15.6 mmol) of 4-chlorobenzoyl chloride and 2.7 ml (19.5 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. stirringwere stirred
  2. temperatureunder cooling with ice for 2 hours
  3. stirringwere stirred at 70° C. for 6 hours
  4. customThe solvent was evaporated
  5. extractionAfter the extraction with ethyl acetate as the extracting solvent by an ordinary method
  6. customthe obtained crude product
  7. temperatureunder cooling with ice, and they
  8. stirringwere stirred
  9. temperatureunder cooling with ice for 2 hours
  10. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-f40e2324f760421ca702df040cf4551f
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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