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

HRID 980962Notes

Reaction equation

HRID 980962 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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),

Sources & evidence

ORD record
ord-6e8d28f70fd74510bfbb7285518f0569
Source dataset
uspto-grants-1987_01
Patent number
US04639441

Reaction notes

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