Dimethylamine → Camptothecin

HRID 275055노트

반응식

HRID 275055 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-42e02c0e42f942e7baf497f5fc548621
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391745

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