Chlorosuccinimide → (R)-2-((2-Chloro-4-(trifluoromethyl)phenyl)amino)-3-methylbutanoic acid

HRID 443464ノート

反応式

HRID 443464 の反応式
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@H:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[Cl:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:19][C:7]1[CH:8]=[C:3]([C:2]([F:17])([F:18])[F:1])[CH:4]=[CH:5][C:6]=1[NH:9][C@H:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12]

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 13388455N-[4-(trifluoromethyl)phenyl]-D-valine

生成物 1

HCID 2316094(R)-2-((2-Chloro-4-(trifluoromethyl)phenyl)amino)-3-methylbutanoic acid

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To 35 ml of carbon tetrachloride are added 2.81 g (10.0 mmol) of (R)-2-(4-trifluoromethylphenylamino)-3-methylbutanoic acid and 1.33 g (9.96 mmol) of N-chlorosuccinimide, and the mixture is heated to reflux for 1 hour. The mixture is worked up by partition between ether/water. The layers are separated and the aqueous phase is extracted with ether (2×). The combined organic extracts are washed with water and with brine, dried over magnesium sulfate, filtered and evaporated, giving (R)-2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoic acid.

後処理

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1 hour
  3. customby partition between ether/water
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with ether (2×)
  6. washThe combined organic extracts are washed with water and with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-5df90869aeeb43d9875121ddb4e74f8e
出典データセット
uspto-grants-1981_04
特許番号
US04260633

反応ノート

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