Potassium Carbonate → cis-3-Phenoxyacetamido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylic acid

HRID 616159Notes

Reaction equation

HRID 616159 reaction equation
C([O-])([O-])=O.[K+].[K+].[O:7]([CH2:14][C:15]([NH:17][C@H:18]1[C:21](=[O:22])[N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])[C@H:19]1[C:34]([O:36]C)=[O:35])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1.O>[O:7]([CH2:14][C:15]([NH:17][C@H:18]1[C:21](=[O:22])[N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])[C@H:19]1[C:34]([OH:36])=[O:35])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 70577439Methyl cis-1-(2,4-Dimethoxybenzyl)-3-phenoxyacetamido-4-oxo-2-azetidinecarboxylate

Product 1

HCID 70577235cis-3-Phenoxyacetamido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of anhydrous K2CO3 (249 mg, 1.8 mmol) in tetrahydrofuran (8 ml) and water (12 ml) is degassed with argon and then methyl cis-3-phenoxyacetamido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate (150 mg, 0.35 mmol) is added. The reaction is stirred 1.5 hours at room temperature, the organic solvent is evaporated and the aqueous layer is acidified and extracted with methylene chloride. The dried extracts are evaporated to give a solid which is recrystallized from ethyl acetate-hexane to give pure cis-3-phenoxyacetamido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylic acid, mp 169°-170° (d).

Workup

  1. customthe organic solvent is evaporated
  2. extractionextracted with methylene chloride
  3. customThe dried extracts are evaporated
  4. customto give a solid which
  5. customis recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-65d159440767475183dced3fcfbf5fc4
Source dataset
uspto-grants-1978_02
Patent number
US04072674

Reaction notes

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