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

HRID 980962ノート

反応式

HRID 980962 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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),

出典と根拠

ORDレコード
ord-6e8d28f70fd74510bfbb7285518f0569
出典データセット
uspto-grants-1987_01
特許番号
US04639441

反応ノート

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