Cornforth reagent → 3-(9,10-Didehydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylurea

HRID 35214

반응식

HRID 35214 반응식
[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][C:10]([N+:18]([O-:20])=[O:19])=[C:11]4[C:17]=3[CH:14]([CH2:15]2)[CH2:13][NH:12]4)=[CH:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.O>[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][C:10]([N+:18]([O-:20])=[O:19])=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)=[CH:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1

참가 물질

5

반응물 2

HCID 2724130Cornforth reagentHCID 867423503-(9,10-Didehydro-2,3-dihydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylurea

생성물 1

HCID 133749593-(9,10-Didehydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylurea수율 46.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

A solution is prepared from 150 mg of 3-(9,10-didehydro-2,3-dihydro-6-methyl-14-nitro-8α-ergolinyl)-1,1-diethylurea in 5 ml of methylene chloride; 250 mg of pyridinium dichromate, dissolved in 2 ml of methylene chloride, is added to the reaction mixture and the latter is agitated for one hour at room temperature. Then the mixture is diluted with water, extracted by shaking with methylene chloride, the organic phase is dried and evaporated. The residue is chromatographed on silica gel with methylene chloride/methanol (5%), thus obtaining 70 mg of 3-(9,10-didehydro-6-methyl-14-nitro-8α-ergolinyl)-1,1-diethylurea.

후처리

  1. additionis added to the reaction mixture
  2. extractionextracted
  3. stirringby shaking with methylene chloride
  4. customthe organic phase is dried
  5. customevaporated
  6. customThe residue is chromatographed on silica gel with methylene chloride/methanol (5%)

출처 및 근거

ORD 기록
ord-ccae881c61ab40a7ad74fdb1aa4f7210
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766128

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