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Propylphosphonic anhydride → Camptothecin

HRID 1068537
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HRID 1068537 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].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]
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참가 물질

6

반응물 3

HCID 111923Propylphosphonic anhydrideHCID 6453552N,N-dimethylpyridin-1-amineHCID 86584209camptothecin TFA

생성물 1

HCID 24360Camptothecin수율 8,851.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e17ba7ea6d124281af76da0b7571ec03
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06251382B1

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