Formic Acid → 9-Aminocamptothecin

HRID 357501

反応式

HRID 357501 の反応式
[CH3:1][CH2:2][C@@:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=[CH:20]2)=[O:11].C(O)=O.C(N(CC)CC)C.C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][CH2:2][C@@:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24]([C:23]([NH2:26])=[CH:22][CH:21]=[CH:20]2)=[CH:25][C:14]=1[CH2:13]3)=[O:11]

参加物

7

反応物 4

HCID 284Formic AcidHCID 297MethaneHCID 8471TriethylamineHCID 472335Rubitecan

生成物 1

HCID 724029-Aminocamptothecin収率 79.6%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

9-nitro camptothecin (3.4 g) was dissolved in distilled DMF (100 ml). Palladium acetate (0.08 g), formic acid (0.95 ml), and triethylamine (3.5 ml) were added. The solution was heated to 80° C., and the heating was continued for 1 hour. DMF (200 ml) and charcoal were added to the reaction mixture, and the stirring was continued for 0.5 hours at 80° C. The mixture was filtered hot through a celite filter aid, and the filtrate was concentrated to small volume. The precipitated orange solid was collected by filtration to yield 2.5 g of 9-amino camptothecin.

後処理

  1. waitthe stirring was continued for 0.5 hours at 80° C
  2. filtrationThe mixture was filtered hot through a celite
  3. filtrationfilter aid
  4. concentrationthe filtrate was concentrated to small volume
  5. filtrationThe precipitated orange solid was collected by filtration

出典と根拠

ORDレコード
ord-09dddc8345924d6c9f07196455a0bc84
出典データセット
uspto-grants-1998_11
特許番号
US05840899

関連ノート

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