70208-19-4Relevant articles and documents
Some Novel Monocyclic cis-β-Lactams from Glycine
Sharma, S. D.,Gupta, P. K.
, p. 760 - 764 (2007/10/02)
Enamine derivatives (Ia, b) obtained by the condensation of glycine and β-dicarbonyl compounds have been utilised for the stereoselective synthesis of cis-β-lactams.Addition of POCl3 to a mixture of the potassium salts (I), imines (IIa-c and III) and triethylamine gives 3-enamino-2-azetidinones (IV, VI, VII, X and XXI) in 30-40 percent yield.Imines (IId and IIe) prepared from ethyl glycinate hydrochloride and aromatic aldehydes, when subjected to this reaction yield 3-enamino-β-lactams (XIII and XVII) carrying an ester function.The protecting β-dicarbonyl function canbe easily removed with ethanol/HCl to generate the α-amino-β-lactams (V, VIII, XI, XIV, XVIII and XXII) which have been used as the progenitors for the preparation of 3-amido-2-azetidinones.The α-amido-β-lactams (XV and XIX) having an ester function on treatment with 0.1 N NaOH in acetone get converted into the novel α-amido-β-lactams (XVI and XX) carrying a free carboxy function essential for antibacterial activity.