Penicillin V → N,N'-Dicyclohexylurea

HRID 1587641

반응식

HRID 1587641 반응식
CC1(C)S[C@@H]2[C@H](NC(COC3C=CC=CC=3)=O)C(=[O:9])N2[C@H]1C(O)=O.CN(C1C=CC=CN=1)C.[CH2:34]1[CH2:39][CH2:38][CH:37]([N:40]=[C:41]=[N:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH2:36][CH2:35]1>C(Cl)Cl>[CH:43]1([NH:42][C:41](=[O:9])[NH:40][CH:37]2[CH2:36][CH2:35][CH2:34][CH2:39][CH2:38]2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

참가 물질

5

반응물 3

HCID 6869Penicillin VHCID 10868DicyclohexylcarbodiimideHCID 218852-Dimethylaminopyridine

생성물 1

HCID 4277N,N'-Dicyclohexylurea

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 10 mL round-bottomed flask, 0.400 g (0.178 mmol) of the poly(PEG-Lys) having ethanolamide pendant functional groups of Example 6 was dissolved in 4 mL of methylene chloride. To this solution was added 0.094 g (0.267 mmol) of Penicillin V (Sigma) and 0.008 g (0.065 mmol) of dimethylaminopyridine (Aldrich). The reaction mixture was cooled in an ice water bath and then 0.048 g (0.232 mmol) of DCC was added. After a few hours at 0° C., the reaction vessel was moved to a cold room maintained at 420 C. and allowed to stir for almost six days. A precipitate of dicyclohexyl urea formed and was removed by filtration. The drug conjugate was precipitated with cold ether. About 0.250 g of crude product was obtained which was purified by reprecipitation twice from isopropanol. TLC in methanol showed absence of free drug.

후처리

  1. temperatureThe reaction mixture was cooled in an ice water bath
  2. waitAfter a few hours at 0° C.
  3. temperaturemaintained at 420 C

출처 및 근거

ORD 기록
ord-cfe48a704ad8418e8623c1335992e307
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05219564

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