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

HRID 35214

反応式

HRID 35214 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-ccae881c61ab40a7ad74fdb1aa4f7210
出典データセット
uspto-grants-1988_08
特許番号
US04766128

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