Triethylamine → HCID 86589880、化合物

HRID 2417507ノート

反応式

HRID 2417507 の反応式
[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]

参加物

12

反応物 7

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

生成物 1

HCID 86589880HCID 86589880、化合物

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4af954bd0bf347cf9d40a3ce2d590776
出典データセット
uspto-grants-2004_11
特許番号
US06825191B2

反応ノート

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