Aniline → 7-Phenyliminomethylcamptothecin

HRID 1356983

반응식

HRID 1356983 반응식
[CH3:1][CH2:2][C@@:3]1([OH:28])[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](=[C:15]([CH:26]=O)[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Yb]>C(Cl)Cl>[CH3:1][CH2:2][C@@:3]1([OH:28])[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](=[C:15]([CH:26]=[N:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]

참가 물질

5

반응물 3

HCID 6115AnilineHCID 23992YtterbiumHCID 1498761H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, (S)-

생성물 1

HCID 98684337-Phenyliminomethylcamptothecin수율 51.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

100 mg (0.26 mmoles) of 7-formylcamptothecin, dissolved into 20 ml of methylene chloride, and 25 μl (0.26 mmoles) of aniline, dissolved into 0.5 ml of methylene chloride, were added to a suspension of ytterbium triphlate (16.5 mg. 0.026 mmoles, 10 % mol) in 5 ml of methylene chloride containing MS 4A and were left 3.5 hours under stirring at room T, then the solvent was evaporated under vacuum. The product was purified by means of flash chromatography on silica gel using a mixture of methylene chloride/methanol 98/2 as eluant. 60 mg of a yellow solid were obtained.

후처리

  1. customthe solvent was evaporated under vacuum
  2. customThe product was purified by means of flash chromatography on silica gel using
  3. additiona mixture of methylene chloride/methanol 98/2 as eluant

출처 및 근거

ORD 기록
ord-ceca403a786e4758ad8483023a9ba01a
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589939B2

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