Water → N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-phenoxycarbonyl-L-valinamide

HRID 2394324

반응식

HRID 2394324 반응식
CN1CC[O:5]CC1.[C:8]([C:10]1[CH:27]=[CH:26][C:13]([O:14][CH2:15][CH:16]([NH:18][C:19](=[O:25])[C@H:20]([CH:22]([CH3:24])[CH3:23])[NH2:21])[CH3:17])=[CH:12][CH:11]=1)#[N:9].[CH:28]1[CH:33]=[CH:32][C:31]([O:34][C:35](Cl)=S)=[CH:30][CH:29]=1.O>C(Cl)Cl>[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH:16]([NH:18][C:19](=[O:25])[C@H:20]([CH:22]([CH3:23])[CH3:24])[NH:21][C:35]([O:34][C:31]2[CH:32]=[CH:33][CH:28]=[CH:29][CH:30]=2)=[O:5])[CH3:17])=[CH:26][CH:27]=1)#[N:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 70498Phenyl thioxochloroformateHCID 22866848N1-[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide

생성물 1

HCID 53713420N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-phenoxycarbonyl-L-valinamide수율 76.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

0.4 g of N-methylmorpholine was added to a suspension containing 1.1 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide suspended in 40 ml of methylene chloride, at -15° C. After 0.7 g of phenyl chlorothionoformate was added to the mixture at -15° C., the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred, and then the whole mixture was stirred for 15 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus yielding 1.2 g of the desired product in the form of a yellow glutinous substance (yield: 75%).

후처리

  1. stirringthe whole mixture was stirred for 15 hours at room temperature
  2. washAfter the methylene chloride layer was washed with water
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customthe methylene chloride was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-d3459f31632b4562aafcf48ee493a05f
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05811424

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