80082-47-9

Upstream product

• 88144-22-3 benzyloxycarbonyl-L-β-chloroalanine amide N-sulfonate tetrabutylammonium salt 
• 86041-08-9 (3S)-(benzyloxycarbonyl)amino-1-trimethylsilyl-2-azetidinone 
• 64319-92-2 (3S)-(benzyloxycarbonyl)amino-α-isopropyl-2-oxoazetidine-1-acetic acid 
• 7625-65-2 L-carbobenzyloxy-β-chloroalanine 
• 80082-81-1 benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 80082-84-4 (3S)-(benzyloxycarbonyl)amino-2-azetidine-1-sulfonic acid, potassium salt 
• 84791-01-5 (3S)-(benzyloxycarbonyl)amino-1-(α-(acetoxy)isobutyl)-2-azetidinone 
• 501-53-1 benzyl chloroformate 

Relevant academic research and scientific papers

2-OXO-1-AZETIDINESULFONIC ACID SALTS

Antibacterial activity is exhibited by beta-lactams having a sulfonic acid salt substituent in the 1-position and an amino or acylamino substituent in the 3-position.

4-alkylated monobactams. Chiral synthesis and antibacterial activity

The synthesis of 4-alkylated monobactams by a variety of procedures is described. Two complementary procedures have been developed for the chiral synthesis of monobactams: (1) sulfonation of 4-alkyl-3-(protected)amino-2-azetidinones with various complexes of SO3; and (2) cyclization of β-mesyloxyacyl sulfamates derived from β-alkyl-β-hydroxy-α-amino acids. The most general procedure involves introduction of the alkyl group via a Grignard reaction on 6-APA-derived sulfones 23 or 24 followed by sulfonation. For the specific case of (3S,trans-)-3-amino-4-methylmonobactamic acid (48), cyclization of the β-mesyloxyacyl sulfamate 40 derived from (L)-threonine is the preferred route. The introduction of 4-alkyl groups into monobactams results in a decrease in activity against gram-positive bacteria, an increase in activity against gram-negative bacteria, and an increase in β-lactamase stability. Increasing the size of the alkyl group beyond methyl results in diminished intrinsic antibacterial activity. 4β-Alkylmonobactams display better β-lactamase stability than their 4α-counterparts.

Monobactams. The Conversion of 6-APA to (S)-3-Amino-2-oxoazetidine-1-sulfonic Acid and Its 3(RS)-Methoxy Derivative

A facile conversion of 6-APA to (S)-3-aminomonobactamic acid (3-AMA) and its 3(RS)-methoxy derivative, key intermediates for the synthesis of 3-(acylamino)-2-oxoazetidine-1-sulfonic acids (monobactams), is described.

Monobactams. Stereospecific Synthesis of (S)-3-Amino-2-oxoazetidine-1-sulfonic Acids

A facile, stereospecific synthesis of 3-amino-2-oxoazetidine-1-sulfonic acids (monobactams) by the cyclization of acyl sulfamates derived from β-hydroxy amino acids is described.

Monobactams. Preparation of (S)-3-Amino-2-oxoazetidine-1-sulfonic Acids from L-α-Amino-β-hydroxy Acids via Their Hydroxamic Esters

The cyclization of the O-methylhydroxamates 13-15 afforded excellent yields of the 1-methoxyazetidinones 16-18.Reductive cleavage of the methoxy group gave N-1-unsubstituted azetidinones 9, 19, and 20 which were sulfonated and deprotected, yielding zwitterions 29-31.These materials serve as general intermediates for the preparation of a large variety of monobactam antimicrobial agents.