74189-25-6

Upstream product

• 24138-28-1 6-bromopenicillanic acid 
• 908093-98-1 diazodiphenylmethane 
• 75527-84-3 diphenylmethyl 6,6-dibromopenicillanate 
• 91-01-0 1,1-Diphenylmethanol 
• 551-16-6 6-Aminopenicillanic Acid 
• 688-73-3 tri-n-butyl-tin hydride 

Downstream Products

• 108834-94-2 benzhydryl 6α-allylpenicillanate 
• 73968-83-9 benzhydryl 6,6-dihydropenicillate 
• 99651-36-2 benzhydryl 6α-bromopenicillanate S,S-dioxide 
• 108834-83-9 benzhydryl 6α-(2'-carbomethoxyethyl)pencillanate 
• 74189-26-7 benzhydryl 6β-(1-hydroxyethyl)penicillanate 
• 89789-07-1 (2S,3S,5R) 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane2-carboxylic acid 4,4-dioxide, diphenyl methyl ester 
• 89786-04-9 tazobactam acid 
• 108834-82-8 benzhydryl 6α-(2'-cyanoethyl)penicillanate 
• 108834-84-0 benzhydryl 6α-(2'-acetoxyethyl)penicillanate 
• 303730-77-0 diphenylmethyl (2S)-2-[(4S)-4-chloro-2-oxazetidin-1-yl]-2-(1-chlorothio-1-methylethyl)-acetate 
• 87579-78-0 diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 
• 89786-04-9 tazobactam 
• 85573-72-4 (R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester 
• 122661-93-2 2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester 

Relevant academic research and scientific papers

Application of Continuous Flow in Tazobactam Synthesis

Tazobactam is a β-lactamase inhibitor. In this work, a combination of continuous flow and batch experiments for the synthesis of tazobactam has been developed. The first three steps and the preparation of the peroxyacetic acid are continuously carried out in the microreactors, which improves the procedure safety and efficiency. There is also a final step of the deprotection reaction in the microreactor, which can increase the yield and reduce the formation of impurities. Under optimized process conditions, the total yield of the target product reached 37.09% (30.93% in batch). The continuous flow method not only greatly reduces the reaction time but also significantly improves procedure safety and increases the yield.

A new approach to the synthesis of tazobactam using an organosilver compound

Tazobactam (9) was synthesized in 8 steps from the readily accessible 6-APA. By the first use of silver triazole as reactant, the formation of the isomer 7 was avoided and a total yield of 50%, which was two to three times higher than that of reported procedures for 9, was obtained. Georg Thieme Verlag Stuttgart.

Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid

Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the s

STEREOSELECTIVE SYNTHESIS OF 6α-HALOPENICILLANATES BY SAMARIUM(II) IODIDE PROMOTED REDUCTION OF 6,6-DIHALOPENICILLANATES

A mild an efficient samarium(II) iodide promoted-reduction of 6,6-dibromopenicillanates for stereoselective synthesis of 6α-bromopenicillanates has been developed.

β-Bromopenicillanic acid sulfone

(2S,5R,6S)-6β-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, S,S-dioxide, physiologically acceptable salts thereof and readily hydrolyzable ester thereof inhibit the action of the β-lactamase enzyme RTEM.