N-Methylpiperidine → N1-[1-(2-Benzothiazolyl)ethyl]-N2-isopropoxycarbonyl-L-valinamide

HRID 481467노트

반응식

HRID 481467 반응식
CN1CCCCC1.[CH:8]([O:11][C:12]([NH:14][C@H:15]([C:19]([OH:21])=O)[CH:16]([CH3:18])[CH3:17])=[O:13])([CH3:10])[CH3:9].ClC(OCC(C)C)=O.[S:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[CH:39]([NH2:41])[CH3:40]>C(Cl)Cl>[S:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[CH:39]([NH:41][C:19](=[O:21])[C@H:15]([CH:16]([CH3:17])[CH3:18])[NH:14][C:12]([O:11][CH:8]([CH3:9])[CH3:10])=[O:13])[CH3:40]

참가 물질

6

반응물 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 11063514(2S)-3-methyl-2-(((propan-2-yloxy)carbonyl)amino)butanoic acidHCID 112061111-(1,3-Benzothiazol-2-yl)ethan-1-amine

생성물 1

HCID 70266697N1-[1-(2-Benzothiazolyl)ethyl]-N2-isopropoxycarbonyl-L-valinamide수율 58.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

0.3 g of N-methylpiperidine was added to a solution containing 0.6 g of N-isopropoxycarbonyl-L-valine dissolved in 40 mL of methylene chloride, at -20° C., and then the mixture was stirred for 10 minutes at the same temperature. 0.4 g of isobutyl chloroformate was added to the mixture at -40° C., and then stirred for 1 hour at -40° C. to -15° C. After 0.5 g of 1-(2-benzothiazolyl)ethylamine was added to this mixture at -60° C. and the refrigerant was put off, the reaction mixture was warmed naturally to room temperature while being stirred. After completion of the reaction, the reaction mixture was washed successively with water, a 5% aqueous solution of sodium bicarbonate, and water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue, which was a crude crystal, was purified by column chromatography on silica gel, thus yielding 0.6 g of the desired product in the form of a white powder (yield: 59%).

후처리

  1. stirringstirred for 1 hour at -40° C. to -15° C
  2. stirringwhile being stirred
  3. customAfter completion of the reaction
  4. washthe reaction mixture was washed successively with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customwas purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-11e180d4e96745e29aaf576ab8848b60
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789428

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