Dicyclohexylcarbodiimide → 3-Benzylpyrrolylmethyl 2-(2-methyl-4-trifluoromethylphenylamino)-3-methylbutanoate

HRID 1413968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1413968
[CH2:1]([C:8]1[CH:12]=[CH:11][NH:10][C:9]=1[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[NH:26][CH:27]([CH:31]([CH3:33])[CH3:32])[C:28](O)=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl.CN(C)C=O>[CH3:15][C:16]1[CH:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:19]=[CH:18][C:17]=1[NH:26][CH:27]([CH:31]([CH3:33])[CH3:32])[C:28]([O:14][CH2:13][C:9]1[NH:10][CH:11]=[CH:12][C:8]=1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:29]

Komponenten

7

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 202893022-(2-Methyl-4-trifluoromethylphenylamino)-3-methylbutanoic acidHCID 543430813-Benzyl-1-pyrrolylmethanol

Produkt 1

HCID 202893043-Benzylpyrrolylmethyl 2-(2-methyl-4-trifluoromethylphenylamino)-3-methylbutanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-benzylpyrrolylmethyl alcohol (1.8 mmol), 2-(2-methyl-4-trifluoromethylphenylamino)-3-methylbutanoic acid (2.0 mmol) and 4-dimethylaminopyridine (0.65 mmol) in 20 ml of methylene chloride and 2 ml of dimethylformamide is added N,N'-dicyclohexylcarbodiimide (2.0 mml). The reaction mixture is stirred, under nitrogen, for two hours and then filtered and extracted with water. The aqueous phase is extracted with ether. The combined organic phases are washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, dried over calcium sulfate and solvent evaporated. The crude product is chromatographed on a rotary chromatograph eluting with 25% ether/hexane to yield 3-benzylpyrrolylmethyl 2-(2-methyl-4-trifluoromethylphenylamino)-3-methylbutanoate.

Aufarbeitung

  1. filtrationfiltered
  2. extractionextracted with water
  3. extractionThe aqueous phase is extracted with ether
  4. washThe combined organic phases are washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  5. dry with materialdried over calcium sulfate and solvent
  6. customevaporated
  7. customThe crude product is chromatographed on a rotary chromatograph
  8. washeluting with 25% ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-100534890eee4f8688de021fe49c0fc2
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04252724

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