Triethylamine → 4-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl-amide]

HRID 654013노트

반응식

HRID 654013 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[C:4]([C:21]([F:24])([F:23])[F:22])[CH:3]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[OH:36][CH:37]([CH:40]1[CH2:44][O:43][C:42]([CH3:46])([CH3:45])[O:41]1)[CH2:38][NH2:39]>C(OCC)(=O)C>[OH:36][CH:37]([CH:40]1[CH2:44][O:43][C:42]([CH3:46])([CH3:45])[O:41]1)[CH2:38][NH:39][C:16](=[O:17])[C:15]1[CH:14]=[CH:13][C:12]([S:9](=[O:11])(=[O:10])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[C:21]([F:22])([F:23])[F:24])=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 11971028alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanolHCID 150576074-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoic acid

생성물 1

HCID 150576084-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl-amide]

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

3.63 g (10 mmol) of 4-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzoic acid is suspended in 36 ml of ethyl acetate, 2.38 g (20 mmol) of thionylchloride is added and the suspension is heated to boiling temperature. After 15 minutes a clear solution is present, after 1 hour the formation of the acid chloride is complete. The solution is evaporated to dryness under reduced pressure, the residue is concentrated by evaporation in a vacuum twice with 50 ml of dichloromethane each and the dissolved in 36 ml of dioxane. 1.21 g (12 mmol) of triethylamine and 1.93 g (12 mmol) of 2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamine are added to this solution and it is stirred for 5 hours at room temperature. The reaction solution is then evaporated to dryness in a vacuum, the residue is extracted with ethyl acetate, the ethyl acetate extract is concentrated by evaporation in a vacuum and the residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane. 3.19 g (6.3 mmol) =63% of the theoretical yield of the product is obtained as an amorphous solid.

후처리

  1. temperaturethe suspension is heated
  2. customThe solution is evaporated to dryness under reduced pressure
  3. concentrationthe residue is concentrated by evaporation in a vacuum twice with 50 ml of dichloromethane each and the
  4. dissolutiondissolved in 36 ml of dioxane
  5. customThe reaction solution is then evaporated to dryness in a vacuum
  6. extractionthe residue is extracted with ethyl acetate
  7. extractionthe ethyl acetate extract
  8. concentrationis concentrated by evaporation in a vacuum
  9. customthe residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane
  10. custom3.19 g (6.3 mmol) =63% of the theoretical yield of the product is obtained as an amorphous solid

출처 및 근거

ORD 기록
ord-1d0ae980b6674998865f7711a5a3a508
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05130119

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