Potassium Hydroxide → p-Nitrobenzyl (4-methylthio-2-azetidinon-1-yl)acetate

HRID 980962노트

반응식

HRID 980962 반응식
[OH-].[K+].[CH3:3][S:4][CH:5]1[NH:8][C:7](=[O:9])[CH2:6]1.I[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:13]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(OCC)(=O)C>[CH3:3][S:4][CH:5]1[N:8]([CH2:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[O:13])[C:7](=[O:9])[CH2:6]1

참가 물질

7

반응물 3

HCID 14797Potassium HydroxideHCID 126772484-(Methylsulfanyl)azetidin-2-oneHCID 13038805p-Nitrobenzyl iodoacetate

생성물 1

HCID 20220761p-Nitrobenzyl (4-methylthio-2-azetidinon-1-yl)acetate수율 25.5%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

Powdery potassium hydroxide (36 mg, 0.64 mmole) and tetrabutylammonium bromide (21 mg) were suspended in tetrahydrofuran (3 ml). To the suspension was slowly added dropwise a solution of 4-methylthio-2-azetidinone (72.5 mg, 0.62 mmole) and p-nitrobenzyl iodoacetate (493 mg, 1.25 mmoles) in tetrahydrofuran (1 ml) at -20° C., with stirring. The temperature of the mixture was elevated to room temperature step by step and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the mixture was diluted with ethyl acetate and subjected to a natural filtration. The filtrate was concentrated under reduced pressure and the resulting residue was purified by preparative thin layer chromatography (eluent: a 1:1 by volume mixture of ethyl acetate and benzene), to give 49 mg of the desired compound as crystals.

후처리

  1. customwas elevated to room temperature
  2. stirringthe mixture was stirred at room temperature for 1.5 hours
  3. customAfter completion of the reaction
  4. filtrationsubjected to a natural filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by preparative thin layer chromatography (eluent
  7. additiona 1:1 by volume mixture of ethyl acetate and benzene),

출처 및 근거

ORD 기록
ord-6e8d28f70fd74510bfbb7285518f0569
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04639441

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