Propylphosphonic anhydride → Camptothecin

HRID 1068537

反応式

HRID 1068537 の反応式
[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].C(O)(C(F)(F)F)=O.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.CN(C)N1C=CC=CC1>C(OCC)(=O)C.ClCCl>[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]

参加物

6

反応物 3

HCID 111923Propylphosphonic anhydrideHCID 6453552N,N-dimethylpyridin-1-amineHCID 86584209HCID 86584209、化合物

生成物 1

HCID 24360Camptothecin収率 8,851.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2.0 g (0.10 mmoles) of m-PEG20k acid, 60 mg (0.06 mmoles) of diaminopimelic camptothecin TFA salt, 0.064 mo (0.10 mmoles) of a 50% solution of 1-propanephosphonic acid cyclic anhydride in ethyl acetate and 25 mg (0.20 mmoles) of N-dimethylamino pyridine in 20 ml of dry dichloromethane was stirred at room temperature overnight followed by washing with 1% aqueous sodium bicarbonate and 0.1N HCl solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation in vacuo. The residue was crystallized from 2-propanol to yield 1.85 g (93% yield)of product.

後処理

  1. washby washing with 1% aqueous sodium bicarbonate and 0.1N HCl solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation in vacuo
  4. customThe residue was crystallized from 2-propanol

出典と根拠

ORDレコード
ord-e17ba7ea6d124281af76da0b7571ec03
出典データセット
uspto-grants-2001_06
特許番号
US06251382B1

関連ノート

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