Dimethylamine → Camptothecin

HRID 260182

반응식

HRID 260182 반응식
[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]

참가 물질

6

반응물 3

HCID 674DimethylamineHCID 6228DimethylformamideHCID 266552Npc28848

생성물 1

HCID 24360Camptothecin수율 91%

시약·촉매·용매 2

HCID 24014Cupric Chloride촉매HCID 977Oxygen용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0a9238a2a36b4aac8a3aaf407c73c113
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05525731

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