134237-56-2

Usage

Uses

Used in Pharmaceutical R&D:
(6R,7R)-Benzhydryl (7-(2-difluoromethylthio)acetamido)-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4,2,0]oct-2-ene-2-carboxylate is used as an impurity intermediate for the development of new pharmaceutical compounds. Its unique structure allows researchers to explore its potential in creating innovative drugs with improved efficacy and safety profiles.
Used in Laboratory R&D:
In addition to its applications in the pharmaceutical industry, (6R,7R)-benzhydryl (7-(2-difluoromethylthio)acetamido)-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4,2,0]oct-2-ene-2-carboxylate is also employed in laboratory research and development. Its complex structure makes it a valuable tool for studying various chemical reactions and processes, contributing to the advancement of scientific knowledge in organic chemistry and related fields.

Synthesis

451 mL ofdichloromethane, 2- (difluoro-methylthio) acetic acid 49.6 g, 144.8 mL pyridine was added to reactorand cooled to -40 ° C. (6R, 7R)-benzhydryl-7-amino-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylatein dichloromethane 1080 mL was added to the reactor and temperature wasmaintained at -25 ° C. After the reactionsolution was cooled below -45 ° C, 42 mL of phosphorous oxychloride in 180.4 mLdichloromethane was added at -15°C and stirred for 30 minutes. After checking completion of the reaction1262.8 ml of purified water, 4.59 ml of 35% hydrochloric acid, 2.7 ml of 50%tetrabutylammonium bromide was added dropwise at 0°C, which in turn stirred for10 minutes. Then, 1262.8 ml of methanol was added at 0°C and stirred for 10 minutes. then separating the layer. 902 mL ethanol added to the filtrate and then stirred for 2 hours at -10 and washed with 360.8 mL of ethanol, and a white or slightly yellow horse crystal component of the vacuum-dried for 10 hours at 40 was added (6R,7R)-benzhydryl (7-(2-difluoromethylthio)acetamido)-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4,2,0]oct-2-ene-2-carboxylate (146.7g, 76%).

Upstream product

• 17028-66-9 6β-(4-toluamido)penicillanic acid 
• 82468-41-5 C₂₉H₂₈N₂O₅S 
• 67978-05-6 C₂₉H₂₆N₂O₄ 
• 68313-81-5 diphenylmethyl (2R,6R,7R)-3-methylene-7-[(4-methylbenzoyl)amino]-8-oxo-5-oxa-1-azabicyclo[4.2.0]octane-2-carboxylate 
• 91177-27-4 7-(N-4-methylbenzamide)-3-(chloromethyl)-8-oxo-5-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 68314-38-5 (6R,7R)-benzhydryl 7-(4-methylbenzamide)-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 91-01-0 1,1-Diphenylmethanol 
• 104101-66-8 diphenylmethyl 6β-(4-toluamido)penicillanate 
• 67977-95-1 diphenylmethyl 6β-(4-toluamido)penicillate 1-oxide 
• 83494-32-0 difluoromethylsulfanyl-acetic acid 
• 1892-31-5 propanethioic acid 

Downstream Products

• 1370637-57-2 C₃₀H₂₈F₂N₃O₆S⁽¹⁺⁾*I^(1-) 
• 1370637-79-8 C₃₃H₃₂F₂N₃O₆S⁽¹⁺⁾*I^(1-) 
• 1370637-82-3 C₃₁H₂₈F₂N₅O₆S⁽¹⁺⁾*I^(1-) 

Relevant academic research and scientific papers

Flomoxef process impurity and preparation method thereof

The invention discloses a flomoxef process impurity and a preparation method of the flomoxef process impurity. The method comprises the following steps: synthesizing an intermediate (6R, 6R, 6R, 6R) from flomoxef sodium; the preparation method comprises the following steps: synthesizing a target impurity intermediate from starting materials including (3R, 7R)-3-(chloromethyl)-7-amino-7-methoxy-8-oxo-5-oxa-1-azabicyclo [4.2. 0] octyl-2-ene-2-carboxylic acid benzhydryl ester, methylthioacetic acid and methylthioacetic acid, and condensing the target impurity intermediate with a side chain 1-hydroxyethyl-5-mercapto-1H-tetrazole sodium salt to obtain the target impurity. Finally, removing a benzhydryl protecting group from titanium tetrachloride to obtain (6R, 7R)-7-(2-methylthio) acetamido)-3-(((1-(2-ethoxyl)-1H-tetrazole-5-yl) sulfur) methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo [4.2. 0] oct-2-ene-2-formic acid; according to the invention, convenience is provided for quality research of flomoxef sodium bulk drugs and preparations, and a detection method and a judgment basis are provided for production and safe medication of flomoxef sodium.

METHOD FOR MANUFACTURING 7alpha-ALKOXYOXACEPHEM INTERMEDIATE COMPOUND

The present disclosure provides a method for preparing a 7α-alkoxyoxacephem intermediate compound, the method comprising a process (S1) including: reacting a compound represented by a following chemical formula 1 with a halogen compound in an organic solv

A method for preparing 1-Oxacephalosporin derivatives

The present invention relates to a novel method for preparing 1-oxacephalosporin derivatives as an intermediate for synthesizing 1-oxacephalosporin which is useful for an antimicrobial. The preparation method of the present invention uses a simple halogenation agent. Accordingly, stability is excellent, and a reaction process is simple, and it is easy to control reaction. Also, reaction time is short so that the method is very efficient. The present invention can improve manufacturing yield of 1-oxacephalosporin which is useful for the antimicrobial.

Design, synthesis and antibacterial activity of novel 1-oxacephem analogs

A series of 1-oxacephem analogs were synthesized and their antibacterial properties against five strains of Gram-positive and Gram-negative bacteria were evaluated in vitro while ceftazidine was selected as control. Some of the tested compounds, compound 12c in particular, showed more active against three selected strains than the standard.