24209-38-9

Usage

Uses

Used in Pharmaceutical Industry:
7-TMCA is used as an intermediate for the synthesis of semi-synthetic antibiotics, such as Cefmetazole (C242850), due to its potent antibacterial activity. This application is significant in the development of new and effective treatments for bacterial infections.
Used in Antibacterial Applications:
7-TMCA is utilized as an active pharmaceutical ingredient in the formulation of antibiotics, specifically cephalosporin-based drugs. Its role in these medications is to combat bacterial infections by disrupting the bacterial cell wall synthesis, ultimately leading to the eradication of the infection.
Used in Research and Development:
In the field of pharmaceutical research and development, 7-TMCA serves as a valuable compound for studying the structure-activity relationships of cephalosporin derivatives. This knowledge aids in the design and development of novel antibiotics with improved properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Quality Control and Standardization:
7-TMCA is employed as a reference compound in the quality control and standardization of cephalosporin-based antibiotics. Its use ensures that the final products meet the required specifications and maintain a consistent level of efficacy and safety.

InChI:InChI=1/C10H12N6O3S2/c1-15-10(12-13-14-15)21-3-4-2-20-8-5(11)7(17)16(8)6(4)9(18)19/h5,8H,2-3,11H2,1H3,(H,18,19)/t5-,8-/m0/s1

Upstream product

• 7440-44-0 pyrographite 
• 111389-99-2 (6R,7R)-Trimethylsilyl 7-[((Trimethylsilyl)oxy)carbonyl]-amino-3-iodomethylceph-3-em-4-carboxylate 
• 13183-79-4 1-methyl-5-mercaptotetrazole 
• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 18686-81-2 1H-tetrazole-5-thiol 
• 957-68-6 7-Aminocephalosporanic acid 
• 31461-04-8 (6R,7R)-Trimethylsilyl 7-(Trimethylsilyl)amino-3-acetoxy methylceph-3-em-4-carboxylate 
• 111390-00-2 (6R,7R)-Trimethylsilyl 7-[((Trimethylsilyl)oxy)carbonyl]-amino-3-acetoxymethylceph-3-em-4-carboxylate 
• 106134-67-2 (6R,7R)-trimethylsilyl 7-(trimethylsilyl)amino-3-iodomethylceph-3-em-4-carboxylate 

Downstream Products

• 77127-98-1 7-<(R)-2-<3-(3,4-diacetoxybenzoyl)-3-methylureido>-2-phenylacetamido>-3-<(1-methyl-1H-tetrazol-5-yl)thiomethyl>-3-cephem-4-carboxylic acid 
• 77119-49-4 7-<(R)-2-<3-(3,4-diacetoxybenzoyl)-3-methylureido>-2-(4-hydroxyphenyl)acetamido>-3-<(1-methyl-1H-tetrazol-5-yl)thiomethyl>-3-cephem-4-carboxylic acid 
• 65085-01-0 (6R)-7t-[2-(2-amino-thiazol-4-yl)-2-(Z)-methoxyimino-acetylamino]-8-oxo-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 102267-65-2 (6R,7R)-7-[[2-(2-amino-4-thiazolyl)-(Z)-2-(1-diphenylmethoxycarbonyl-1-methylethoxy)imino]acetamido]-3-[[(1-methyl-1H-5-tetrazolyl)thio]-methyl]-3-cephem-4-carboxylic acid 
• 60445-97-8 (6R)-7t-(3,5-di-tert-butyl-4-hydroxy-benzylideneamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; benzyl-trimethyl-ammonium salt 
• 67366-03-4 C₁₇H₁₆N₆O₃S₃ 
• 65052-57-5 7β-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido>-3-<(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl>-ceph-3-em-4-carboxylic acid 
• 77527-71-0 4-<<2-carboxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-7β-yl>amino>-1-benzylpyridinium hydroxide inner salt 
• 80706-34-9 4-<<3-<<(1-methyltetrazol-5-yl)thio>methyl>-2-carboxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-7β-yl>amino>-1-(4-fluorobenzyl)pyridinium hydroxide inner salt 
• 77527-78-7 C₂₃H₂₃N₇O₄S₂ 
• 80730-68-3 C₂₃H₂₀N₈O₃S₂ 
• 80730-67-2 C₂₄H₂₅N₇O₅S₂ 
• 77527-61-8 C₂₂H₂₁N₇O₃S₂ 
• 80730-66-1 C₂₃H₂₃N₇O₃S₂ 

Relevant academic research and scientific papers

New adaptation diseases of cefoperazone medicinal preparation for treating endometritis and other gynecological genital tract infections

The invention discloses new adaptation diseases of cefoperazone medicinal preparation for treating gynecological genital tract infections of gynecology department. The cefoperazone sodium provided bya specific raw material production process is extremely low in impurity content and remarkable in medicine effect, so that the quality of a preparation product is improved, the safety and effectiveness of the preparation product are guaranteed, and the invention provides the application of preparing the medicine for treating endometritis and other gynecological genital tract infections.

1/4 head spore Meng Duozhi sodium compound (by machine translation)

The invention discloses 1/4 head spore Meng Duozhi sodium compound and its preparation method, each of the plurality of containing sodium molar spore Meng 1/4 mole water. The method of the invention for preparing the compounds of the spore Meng Duozhi sodium, low impurity content, good stability, and good fluidity, the moisture and small, with more extensive application prospects. (by machine translation)

1/5 water cefamandole sodium compound

The invention discloses a 1/5 water cefamandole sodium compound and a preparation method thereof. Each mol of cefamandole sodium compound contains 1/5 mol of water. The cefamandole sodium compound prepared by the method disclosed by the invention has low impurity content and good stability and has a wider application prospect.

Preparation method of cefmetazole

The invention relates to a preparation method of cefmetazole. The preparation method comprises the steps of adopting a one-pot method containing 7-ACA, 1-methyl-5-tetrazole-thione and chloroacetyl chloride, obtaining 7-DCT, then using seven-position methoxy groups of sodium methylate and tert-butyl hypochlorite, and obtaining methoxy cephalosporin mother nuclei which are shared mother nuclei. The cefmetazole can serve as four methoxy cephalosporin products, namely cefminox, cefmetazole, cephalosporin and cefotetan disodium, three steps are omitted, the processing steps are greatly shortened, cost is lowered, and the overall yield is raised to 70%.

A novel synthetic route to 7-MAC from 7-ACA

An efficient and practical seven-step procedure is described for the synthesis of (6R,7S)-benzhydryl-7-amino-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-aza-bicyclo [4.2.0]oct-2-ene-2-carboxylate (7-MAC, 3) with overall yield of 49?%. This synthesis features a convenient and highly selective method for the introduction of 7α-methoxy group to cephalosporin nucleus in 10 using MeOLi/t-BuOCl in THF.

Synthesis method of methoxy cephalosporin drug intermediate 7-MAC

The invention provides a synthesis method of a methoxy cephalosporin drug intermediate 7alpha-methoxy-7beta-amino-3-(1-methyl-1H-tetrazole-5-methylthio)-3-cephem-4-diphenylmethyl carboxylate (7-MAC). The synthesis method comprises steps as follows: 7-aminocephalosporanic acid (7-ACA) is taken as a raw material, a side chain at a C-3 site and amino at a C-7beta site are modified firstly, oxidative rearrangement and reduction are performed after protection of diphenylmethyl at a C-4 site, a methoxy group is selectively introduced to a C-7alpha site, an amino protecting group is removed finally, and 7-MAC is obtained through 7-step reaction. According to the synthesis method of the methoxy cephalosporin drug intermediate 7-MAC, the defects that byproducts such as methyl mercaptan and the like are required to be removed while the methoxy group is introduced in the existing synthesis technology are overcome. Meanwhile, the synthesis method of the methoxy cephalosporin drug intermediate7-MAC does not adopt diazo compounds, and accordingly, danger such as explosion possibly caused by the diazo compounds is eliminated.

Preparation method for sodium cefamandole

The invention relates to a preparation method for sodium cefamandole. The preparation method comprises mixing 7-aminocephalosporanic acid, 5-mercapto-1-methyltetrazole and a catalyst boron trifluoride acetonitrile complex, heating and stirring for reacting, cooling and processing to obtain a compound 1; performing heating refluxing reaction on the compound 1 and a silanization agent until the solution is clear, adding N,N-dimethylaniline under protection of inert gas, and dropwise adding (D)-(-)-O-formylmandeloyl chloride for chloroformylation reaction, after the reaction is finished, adding water for hydrolysis, adjusting the pH value to 5.0-7.5 by using a sodium bicarbonate or sodium carbonate solution, separating out the organic layer, adding ethyl acetate into the water layer, and adjusting the pH value to 0.5-1.5, so as to obtain a cephamandole solution, performing decoloring and dewatering, then adding an organic solution of sodium isooctanoate or sodium acetate, and crystallizing to obtain sodium cefamandole. The preparation technology is simple and easy to realize, the obtained product is shallow in color grade, impurity is less, yield is high, and the solvent is easy to recover and reuse, and thus production cost is reduced.

Process for preparing cephalosporin intermediates

Processes for the preparation of stable, crystalline cephalosporin intermediates of the formula STR1 wherein X is HI or HCl, and Nu and Nu≈ are certain N-containing heterocyclic rings attached via a sulfur atom or a ring nitrogen atom, respectively, which are substantially free of the Δ2 isomer; processes for intermediates in the preparation of the above compounds; and processes for the preparation of broad-spectrum cephalosporin antibiotics.

Cycloaddition reactions of cephalosporin compounds. XI [1]. 1,3-dipolar cycloaddition reaction of an exo-2-methylenecephem with diphenyldiazomethane

In the 1,3-dipolar cycloaddition reaction of the exo-2-methylenecephem 6 with diphenyldiazomethane the initially formed pyrazolines decompose and spirocyclopropylcephalosporin formation takes place. The structure elucidation with 1H, 13C, ASIS and NOE nmr methods is also described.

Use of Bistrimethylsilylated Intermediates in the Preparation of Semisynthetic 7-Amino-3-substituted-cephems. Expedient Syntheses of a New 3-cephalosporin

Several "one-pot" methods for conversion of 7-ACA (6) to a variety of 7-amino-3-(ammoniomethyl)- or 7-amino-3-methyl>cephalosporin derivatives via bistrimethylsilylated intermediates are presented.For example, bistrimethylsilylation of 7-ACA (6) in 1,1,2-trichlorotrifluoroethane (Freon TF) using HMDS and 3 mol percent TMSI, followed by treatment with 1.15 equiv of TMSI and subsequent reactions with tertiary alicyclic or heteroaromatic amines or heteroaromatic thiols, led to the desired products in good yields.Alternatively, novel reaction of the bistrimethylsilylated derivative 15 with amine/TMSI adducts in Freon TF at 35 deg C provided an alternative approach to some 7-amino-3-(ammoniomethyl)cephalosporins.The solvent dependence of Δ3/Δ2 isomer ratios in quaternization reactions of 11 with N-methylpyrrolidine is presented.Hypotheses for the explanation of experimental results observed on reaction of 15 in Freon TF with amine/TMSI adducts are presented.Acylation of 17 (X = Cl, I) with 8 in aqueous THF provided 18 (BMY-28142) as its sulfate salt in overall yields of 18percent and 43percent, respectively, from 7-ACA (6).