930-21-2Relevant articles and documents
AN EFFICIENT β-AMINO ACID CYCLODEHYDRATION USING METHANESULFONYL CHLORIDE TO THIENAMYCIN INTERMEDIATE 3--4--AZETIDIN-2-ONE
Loewe, M. F.,Cvetovich, R. J.,Hazen, G. G.
, p. 2299 - 2302 (1991)
A new process for β-amino acid 1 cyclodehydration to β-lactam 2 using methanesulfonyl chloride/ sodium bicarbonate is described.
Method for synthesizing 2-azetidinone
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Paragraph 0019-0028; 0029-0038; 0039-0048, (2018/06/26)
The invention discloses a method for synthesizing 2-azetidinone in the technical field of chemical synthesis. The method comprises specific steps as follows: S1, preparation of a mixed solution; S2, addition of an aid and dilution; S3, solution extraction and drying; S4, addition of sodium hydroxide and heating; S5, solution neutralization, water washing and drying; S6, toluene dissolution; S7, detection with a chromatograph; S8, product purification treatment. The synthesis method is simple, the prepared finished product has high accuracy, the temperature and the reaction time are controllable in the synthesis process, no raw material waste phenomenon is caused in the synthesis process and the method is suitable for large-scale production in a factory.
Suppressed β-effect of silicon in 3-silylated monocyclic β-lactams: The role of antiaromaticity
Bag, Subhendu Sekhar,Kundu, Rajen,Basak, Amit,Slanina, Zdenek
supporting information; experimental part, p. 5722 - 5725 (2010/03/01)
[Chemical Equation Presented] The β-stabilizing effect of silicon substituent at C-3 on a C-4 cation and a radical In the 2-azetidinone systems is studied using NMR kinetics. While the β-effect Is virtually nonexistent in the case of a cation, a foiled β-effect (only a 3-fold rate enhancement) Is observed for a radical intermediate. From both the experimental and theoretical studies, It Is demonstrated that antiaromaticity Is playing the prime role In suppressing the β-stabilizing effect of silicon.
Competitive endo- and exo-cyclic C-N fission in the hydrolysis of N-aroyl β-lactams
Tsang, Wing Y.,Ahmed, Naveed,Hemming, Karl,Page, Michael I.
, p. 1432 - 1439 (2007/10/03)
The balance between endo- and exo-cyclic C-N fission in the hydrolysis of N-aroyl β-lactams shows that the difference in reactivity between strained β-lactams and their acyclic analogues is minimal. Attack of hydroxide ion occurs preferentially at the exocyclic acyl centre rather than that of the β-lactam during the hydrolysis of N-p-nitrobenzoyl β-lactam. In general, both endo- and exo-cyclic C-N bond fission occurs in the alkaline hydrolysis of N-aroyl β-lactams, the ratio of which varies with the aryl substituent. Hence, the Bronsted β-values differ for the two processes: -0.55 for the ring-opening reaction and -1.54 for the exocyclic C-N bond fission reaction. For the pH-independent and acid-catalysed hydrolysis of N-benzoyl β-lactam, less than 3% of products are derived from exocyclic C-N bond fission.
