Triethylamine → HCID 86589880, compound

HRID 2417507Notes

Reaction equation

HRID 2417507 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=O)=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].CS(Cl)(=O)=O.Cl.[CH2:38]([O:40][C:41](=[O:44])[CH2:42][NH2:43])[CH3:39].C(=O)([O-])O.[Na+]>C1COCC1.ClCCl.C(O)C.C(OCC)(=O)C>[CH2:38]([O:40][C:41](=[O:44])[CH:42]([CH2:7][C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:16])([F:15])[F:1])=[CH:4][C:5]=1[N+:12]([O-:14])=[O:13])[NH2:43])[CH3:39]

Participants

12

Reactant 7

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 6420962-Nitro-4-(trifluoromethyl)benzoic acidHCID 2723640Glycine ethyl ester, hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 86589880HCID 86589880, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g (21 mmol) of 4-trifluoromethyl-2-nitrobenzoic acid was dissolved in a mixture of 200 ml of THF and 4.4 ml (31.5 mmol) of triethylamine. 2.6 ml (28 mmol) of ethyl chloroformate was added to the obtained solution under cooling with ice, and they were stirred for 15 minutes. Precipitates thus formed were removed by the suction filtration. A piece of ice was added to the obtained filtrate, and then 1.6 g (42 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. 1.96 ml (25.2 mmol) of methanesulfonyl chloride and 4.4 ml (31.5 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, the obtained crude product was dissolved in 100 ml of ethanol. 5.9 g (42 mmol) of glycine ethyl ester hydrochloride and 5.3 g (16.1 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70□ for 6 hours. The solvent was evaporated. After the extraction with ethyl acetate, the extract was washed with 1 N hydrochloric acid. The obtained aqueous layer was made basic with 1 N sodium hydroxide. After the extraction with ethyl acetate, the obtained organic layer was washed with saturated aqueous sodium chloride solution and then dried. The solvent was evaporated to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. customPrecipitates thus
  3. customformed
  4. customwere removed by the suction filtration
  5. additionA piece of ice was added to the obtained filtrate
  6. temperatureunder cooling with ice
  7. customwas elevated to room temperature
  8. stirringthe obtained mixture was stirred overnight
  9. stirringwere stirred
  10. temperatureunder cooling with ice for 2 hours
  11. stirringwere stirred at 70□ for 6 hours
  12. customThe solvent was evaporated
  13. extractionAfter the extraction with ethyl acetate
  14. washthe extract was washed with 1 N hydrochloric acid
  15. extractionAfter the extraction with ethyl acetate
  16. washthe obtained organic layer was washed with saturated aqueous sodium chloride solution
  17. customdried
  18. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4af954bd0bf347cf9d40a3ce2d590776
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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