115887-91-7Relevant articles and documents
Preparation method of amino-2-methyl-4-oxo-1-azetidinesulfonic acid intermediate
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, (2020/08/25)
The invention discloses a preparation method of an amino-2-methyl-4-oxo-1-azetidinesulfonic acid intermediate, comprising the following steps: S1, adding N-carbobenzoxy-L-threonine amide into a reaction vessel, adding an organic solvent, stirring, mixing, adding 2-methylpyridine and methylsulfonyl chloride, heating, and carrying out a thermal reaction to obtain a reaction solution I; S2, cooling the reaction solution I to below 0 DEG C, then adding chlorosulfonic acid into the cooled reaction solution I, heating, carrying out a thermal reaction to obtain a reaction solution II, and cooling; and S3, adding deionized water into the cooled reaction solution II for a quenching reaction, then adding alkali liquor into the reaction system to adjust the pH, heating, and carrying out a thermal reaction. The method adopts a one-pot method for synthesis, is simple in process operation and short in period, avoids the generation of three wastes, and realizes the production of a green process; thepurity of the obtained amino-2-methyl-4-oxo-1-azetidinesulfonic acid intermediate is as high as 98.5%, the molar yield is as high as 80.9%, the product quality is good, and the method is suitable forindustrial production.
Ammonia curved the monocyclic parent nucleus method for the preparation of
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, (2017/01/26)
The invention relates to a preparation of Aztreonam monocyclic parent nucleus method, in the method using benzyl chloroformate under strongly acidic conditions the protection, the sodium carbonate is used to carry out closed-loop reaction, the reaction is stable, is greatly improved yield, total yield of 48% the advantages.
Process and intermediates for beta-lactams having aminothiazole(iminooxyacetic acid)acetic acid sidechains
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, (2008/06/13)
Disclosed herein are processes for preparing a compound of the formula STR1 in which a novel compound of the formula STR2 is reacted with a beta lactam of the formula STR3 by treatment with a base, wherein the symbols are as defined in the specification.
Stereoselective synthesis of cis-4-(substituted) monobactams from ethyl acetoacetate
Fernandez-Resa, Piedad,Herranz, Rosario,Conde, Santiago,Arribas, Enrique
, p. 67 - 71 (2007/10/02)
The stereoselective synthesis of cis-3-amino-4-methyl-2-oxoazetidine-1-sulphonic acid (25) from ethyl acetoacetate is described. Nitrosation of this compound and reduction of the resulting oxime gave the corresponding amine, which after treatment with different acyl halides, yielded the acylamino derivatives (6)-(8). Condensation with p-anisidine gave the enamines (12)-(14), which were then reduced to the β-amino acid esters (15)-(17). Stereoselective cyclization with Grignard reagents as base, and appropriate deprotection and sulphonation of the resulting β-lactams (18)-(20), led to the title compounds.
Enantioselective Synthesis of (3S)-trans-4-(Substituted Methyl)monobactams from 2,3-O-Isopropylidene-D-glyceraldehyde
Herranz, Rosario,Conde, Santiago,Fernandez-Resa, Piedad,Arribas, Enrique
, p. 649 - 656 (2007/10/02)
The enantioselective synthesis of various (3S)-trans-4-(substituted methyl)-2-oxoazetidine-1-sulphonic acid derivatives from 2,3-O-isopropylidene-D-glyceraldehyde is described.Reaction of this aldehyde with trimethylsilyl cyanide gave a 80:20 ratio of the corresponding threo and erythro α-amino-nitriles, which by amino protection and subsequent treatment with basic hydrogen peroxide provided the corresponding α-amino carboxamides.Successive selective protection, activation, sulphonation and, finally, stereospecific cyclization of the threo α-carboxamide yielded (2S,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid, an intermediate for the synthesis of the corresponding 4-acyloxymethyl-, 4-carbamoyloxymethyl-, 4-methylsulphonyloxy-methyl-, 4-iodomethyl-, and 4-methyl-2-oxozetidines.
