Nitric Acid → Rubitecan

HRID 564696

반응식

HRID 564696 반응식
[CH3:1][CH2:2][C@@:3]1([OH:26])[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].[N+:27]([O-])([OH:29])=[O:28]>S(=O)(=O)(O)O>[CH3:1][CH2:2][C@@:3]1([OH:26])[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:15][C:14]=1[CH2:13]3)[C:17]([N+:27]([O-:29])=[O:28])=[CH:18][CH:19]=[CH:20]2)=[O:11]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 24360Camptothecin

생성물 1

HCID 472335Rubitecan

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

Camptothecin (25 g) in concentrated sulfuric acid (500 mL) was cooled in an ice-bath. To it was then added 70% nitric acid (30 mL), drop-wise to control the reaction temperature. The reaction mixture was then stirred for 36 hours, poured into excess crushed ice and the organic portion was extracted out using chloroform. The combined organic fraction was washed with freshly prepared 10% sodium bicarbonate solution and brine, and then dried over anhydrous sodium sulfate. Solvent was removed and the residue was purified by flash silica gel column using hexane/ethyl acetate (1:1) as eluent to furnish 2.7 g of 9-nitrocamptothecin.

후처리

  1. additionpoured
  2. custominto excess crushed ice
  3. extractionthe organic portion was extracted out
  4. washThe combined organic fraction was washed with freshly prepared 10% sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customSolvent was removed
  7. customthe residue was purified by flash silica gel column

출처 및 근거

ORD 기록
ord-cfa7149741544fb4a517ea3a14b046a3
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169080A

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