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

HRID 1413968노트

반응식

HRID 1413968 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-100534890eee4f8688de021fe49c0fc2
출처 데이터셋
uspto-grants-1981_02
특허 번호
US04252724

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