Dimethylamine → Camptothecin

HRID 275055

反応式

HRID 275055 の反応式
[CH3:1][CH2:2][CH:3]1[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[C:14](=[CH:15][C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11].CNC.CN(C=[O:33])C>O=O.[Cu](Cl)Cl>[CH3:1][CH2:2][C@@:3]1([OH:33])[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]=[CH:18][CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11]

参加物

6

反応物 3

HCID 674DimethylamineHCID 6228DimethylformamideHCID 266552Npc28848

生成物 1

HCID 24360Camptothecin収率 91%

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 977Oxygen溶媒

実験手順

To a solution of 18 (47.8 mg, 0.144 mmol), copper(II) chloride (80 mg) and dimethylamine (100 μl ) in DMF (16 mL) was bubbled in oxygen for 7 h. The reaction mixture was concentrated in vacuum to about 5 mL, and was then diluted with water. .A solution of saturated ammonium chloride was used to adjusted the pH of the above mixture to about 6, and the resulting mixture was extracted with chloroform (10 mL×10). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 2% methanol in chloroform to give dl-camptothecin (45.5 mg, 91%).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuum to about 5 mL
  2. additionwas then diluted with water
  3. extractionthe resulting mixture was extracted with chloroform (10 mL×10)
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed with 2% methanol in chloroform

出典と根拠

ORDレコード
ord-42e02c0e42f942e7baf497f5fc548621
出典データセット
uspto-grants-1995_02
特許番号
US05391745

関連ノート

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