Propanal → 7-Ethyl-10-Hydroxycamptothecin

HRID 1781303

反応式

HRID 1781303 の反応式
[CH3:1][CH2:2][C@@:3]1([OH:27])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[C:18]([OH:26])[CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11].[CH:28](=O)[CH2:29]C.S(=O)(=O)(O)O.FC(F)(F)C(O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[CH3:28][CH2:29][C:15]1[C:14]2[CH2:13][N:12]3[C:10](=[O:11])[C:5]4[CH2:6][O:7][C:8]([C@:3]([OH:27])([CH2:2][CH3:1])[C:4]=4[CH:25]=[C:24]3[C:23]=2[N:22]=[C:21]2[C:16]=1[CH:17]=[C:18]([OH:26])[CH:19]=[CH:20]2)=[O:9]

参加物

8

反応物 5

HCID 527PropanalHCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 24412Potassium PersulfateHCID 97226Hydroxycamptothecin

生成物 1

HCID 1048427-Ethyl-10-Hydroxycamptothecin

試薬・触媒・溶媒 2

HCID 62662Ferrous sulfate heptahydrate触媒HCID 962Water溶媒2 回

実験手順

The 10-hydroxy camptothecin (800 mg; 2.2 mmol) is suspended in water (24 ml). Iron (II) sulfate heptahydrate (250 mg, 0.85 millimoles) is added to the suspension and then followed by the addition of propionaldehyde (3 ml). The reaction mixture is then cooled in an ice bath and concentrated sulfuric acid (1 ml) and trifluoroacetic acid (24 ml) are added. After stirring the homogeneous solution for 15 minutes, potassium persulfate (3.5 g; 6 mol equivalent) is added, and the mixture is slowly warmed to room temperature. After approximately 15 hours, the reaction mixture is diluted with water and the product is extracted using excess chloroform. The crude product is washed thrice with 5% methanol in ether and dried to obtain 806 mg of the desired compound.

後処理

  1. temperatureThe reaction mixture is then cooled in an ice bath
  2. waitAfter approximately 15 hours
  3. extractionthe product is extracted
  4. washThe crude product is washed thrice with 5% methanol in ether
  5. customdried

出典と根拠

ORDレコード
ord-ce1330cec512459bbd1a23148a42b7c2
出典データセット
uspto-grants-1997_05
特許番号
US05633260

関連ノート

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