74694-53-4

Upstream product

• 74694-50-1 4(S)-4-iodomethyl-azetidin-2-one 
• 52709-42-9 benzylglyoxylate 
• 87692-25-9 benzyl glyoxalate monohydrate 

Downstream Products

• 95336-26-8 (N'-tert-Butoxycarbonyl-hydrazino)-((S)-2-iodomethyl-4-oxo-azetidin-1-yl)-acetic acid benzyl ester 
• 95336-31-5 benzyl 4-t-butoxycarbonyl-8-oxo-1,3,4-triazabicyclo<4.2.0>oct-2-ene-2-carboxylate 

Relevant academic research and scientific papers

Total Synthesis of Analogues of the &β-Lactam Antibiotics. Part 1. Isoclavam-3-carboxylates

4-Hydroxymethylazetidin-2-one (15a), prepared from 4-vinylazetidin-2-one (16) by reductive ozonolysis, was converted into 4-iodomethylazetidin-2-one (15c) by sequential reactions involving toluene-p-sulphonyl chloride and sodium iodide.Compound (15c) reacted with methyl glyoxylate hydrate in the presence of triethylamine to give methyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate (13b) as a 1 : 1 mixture of diastereoisomers, which was transformed into methyl 7-oxo-3-oxa-1-azabicyclo-heptane-2-carboxylate (12a), as a single exo-diastereoisomer, by the action of sodium hydride.The t-butyl, p-nitrobenzyl, and benzyl esters of 7-oxo-3-oxa-1-azabicycloheptane-2-exo-carboxylic acid,i.e. (12d-f), were similarly prepared.Brief treatment of the t-butyl ester (12d) with trifluoroacetic acid resulted in β-lactam cleavage to give (2-t-butoxycarbonyl-3-trifluoroacetyloxazolidin-4-yl)acetic acid (19c) which reacted further with trifluoroacetic acid to give (2-carboxy-3-trifluoroacetyloxazolidin-4-yl)acetic acid (19d).Hydrogenolysis of the benzyl ester (12f), in the presence of sodium hydrogen carbonate, afforded the sodium salt (12b) which underwent rapid β-lactam cleavage in aqueous solution.

Synthesis of 7-Oxo-3-oxa-1-azabicycloheptane-2-carboxylates: Analogues of Clavulanic Acid

4-Iodomethylazetidin-2-one is converted into the title compounds when treated sequentially with glyoxylic acid esters and sodium hydride.