Water → HCID 14209146, compound

HRID 279777Notes

Reaction equation

HRID 279777 reaction equation
C([O:3][C:4]([CH:6]1[CH2:9][C:8](=[O:10])[N:7]1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[O:20][CH3:21])=[O:5])C.[OH-].[Na+].O>C(O)C>[CH3:21][O:20][C:13]1[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:12]=1[CH2:11][N:7]1[C:8](=[O:10])[CH2:9][CH:6]1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13505933HCID 13505933, compound

Product 1

HCID 14209146HCID 14209146, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.80 g (0.020 mole) of ethyl-[1-(2,4-dimethoxy-benzyl)-4-oxo-2-azetidine-carboxylate] in 25 ml of ethanol a solution of 0.88 g (0.022 mole) of sodium hydroxide and 60 ml of water is added. The reaction solution is stirred for 2 hours and extracted three times with 20 ml of ether each. The aqueous layer is acidified to pH 2 with concentrated aqueous hydrochloric acid and extracted three times with 20 ml of dichloromethane each. The united organic solutions are dried over anhydrous magnesium sulfate, filtered and from the filtrate the dichloromethane is distilled off. The residue is treated with ether, the yellowish-white crystalline product is filtered off and recrystallized from benzene. Thus 4.0 g of 1-(2,4-dimethoxy-benzyl)-4-oxo-2-azetidine-carboxylic acid are obtained. Yield: 75.4%. M.p.: 124°-125° C.

Workup

  1. extractionextracted three times with 20 ml of ether each
  2. extractionextracted three times with 20 ml of dichloromethane each
  3. dry with materialThe united organic solutions are dried over anhydrous magnesium sulfate
  4. filtrationfiltered and from the filtrate the dichloromethane
  5. distillationis distilled off
  6. additionThe residue is treated with ether
  7. filtrationthe yellowish-white crystalline product is filtered off
  8. customrecrystallized from benzene

Sources & evidence

ORD record
ord-eaac1cbff3774d55943b3b5b91e2ef6c
Source dataset
uspto-grants-1986_05
Patent number
US04587049

Reaction notes

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