74694-54-5

Basic information

• Product Name: p-nitrobenzyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate
• Synonyms: p-nitrobenzyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate
• CAS NO: 74694-54-5
• Molecular Weight: 420.161
• Mol File: 74694-54-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: p-nitrobenzyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: p-nitrobenzyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate(74694-54-5)
• EPA Substance Registry System: p-nitrobenzyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate(74694-54-5)

Safety Data

• Hazardous Substances Data: 74694-54-5(Hazardous Substances Data)

Upstream product

• 74694-50-1 4(S)-4-iodomethyl-azetidin-2-one 
• 64370-35-0 p-nitrobenzyl glyoxylate 
• 64370-36-1 p-nitrobenzyl α-ethoxy-α-hydroxyacetate 

Downstream Products

• 123176-61-4 p-nitrobenzyl 4-t-butoxycarbonyl-8-oxo-1,2,4-triazabicyclo<4.2.0>oct-2-ene-2-carboxylate 
• 123176-59-0 (N'-tert-Butoxycarbonyl-hydrazino)-((S)-2-iodomethyl-4-oxo-azetidin-1-yl)-acetic acid 4-nitro-benzyl ester 
• 76641-21-9 p-nitrobenzyl isopenam-3-endo-carboxylate 
• 76641-21-9 p-nitrobenzyl isopenam-3-exo-carboxylate 
• 95541-77-8 3-exo-carboxyisopenam 2,2-dioxide p-toluidine salt 
• 76657-05-1 3-exo-p-nitrobenzyloxycarbonylisopenam 2,2-dioxide 
• 95541-75-6 Chloro-(2-iodomethyl-4-oxo-azetidin-1-yl)-acetic acid 4-nitro-benzyl ester 
• 74694-58-9 p-nitrobenzyl 7-oxo-3-oxa-1-azabicyclo<3.2.0>heptane-2-exo-carboxylate 
• 619-73-8 4-nitrobenzyl chloride 
• 95541-75-6 Chloro-((S)-2-iodomethyl-4-oxo-azetidin-1-yl)-acetic acid 4-nitro-benzyl ester 

Relevant articles and documents

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.