Ethyl Acetate → (2R,3R)-4-Oxo-3-(2-phenoxyacetamido)azetidine-2-carboxylic acid

HRID 867227Notes

Reaction equation

HRID 867227 reaction equation
[O:1]([CH2:8][C:9]([NH:11][C@H:12]1[C:15](=[O:16])[NH:14][C@H:13]1[C:17]([O:19]C)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CO.O>[O:1]([CH2:8][C:9]([NH:11][C@H:12]1[C:15](=[O:16])[NH:14][C@H:13]1[C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 53649703Methyl cis-3-phenoxyacetamido-4-oxoazetidine-2-carboxylate

Product 1

HCID 54209443(2R,3R)-4-Oxo-3-(2-phenoxyacetamido)azetidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Methyl cis-3-phenoxyacetamido-4-oxoazetidine-2-carboxylate is treated with K2CO3 in methanol-water as above to give cis-3-phenoxyacetamido-4-oxoazetidine-2-carboxylic acid, mp 150°-51° from ethyl acetate.

Sources & evidence

ORD record
ord-16633fdac9944b3e804b8f666b5e2fab
Source dataset
uspto-grants-1978_07
Patent number
US04103086

Reaction notes

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