37539-03-0

Basic information

• Product Name: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid
• Synonyms: 7-TACA;7-AMINO-3-(1,2,3-TRIAZOL-4-YLTHIO)METHYL CEPHALOSPORANIC ACID;7-AMINO-3-(1,2,3-TRIAZOL-4-YLTHIO)METHYL CEPHALOSPORANIC ACID(7-TACA);7-Amino-3-((1,2,3-Triazol-5-YL)Thiomethyl)Cephalos;(7R)-7-AMINO-3-[(1H-1,2,3-TRIAZOL-4-YLSULFANYL)METHYL]-3,4-DIDEHYDROCEPHAM-4-CARBOXYLIC ACID;(6R-trans)-7-Amino-8-oxo-3-[(1H-1,2,3-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-Amino-3-((1H-1,2,3-triazol-5-yl)-thiomethyl)-ceph-3-em-4-carboxylic acid;TACA
• CAS NO: 37539-03-0
• Molecular Formula: C₁₀H₁₁N₅O₃S₂
• Molecular Weight: 313.36
• EINECS: 253-547-4
• Product Categories: Organic acids
• Mol File: 37539-03-0.mol

Chemical Properties

• Boiling Point: 723.3 °C at 760 mmHg
• Flash Point: 391.2 °C
• Appearance: /
• Density: 1.8g/cm³
• Vapor Pressure: 5.85E-22mmHg at 25°C
• Refractive Index: 1.798
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly, Heated, Sonicated), Water (Slightly)
• PKA: 2.56±0.50(Predicted)
• Stability: Light Sensitive, Temperature Sensitive, Unstable in Solution
• CAS DataBase Reference: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid(37539-03-0)
• EPA Substance Registry System: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid(37539-03-0)

Safety Data

• Hazardous Substances Data: 37539-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid is used as an intermediate in the synthesis of triazole-based semi-synthetic cephalosporins for the development of new antibiotics. These semi-synthetic cephalosporins exhibit improved potency, stability, and effectiveness against a wider range of bacterial infections, making them valuable in the treatment of various diseases caused by resistant bacteria.
Additionally, this compound may also be utilized in research and development for the creation of novel cephalosporin derivatives with enhanced properties, such as increased bioavailability, reduced side effects, and targeted delivery to specific sites of infection.

InChI:InChI=1/C10H11N5O3S2/c11-6-8(16)15-7(10(17)18)4(3-20-9(6)15)2-19-5-1-12-14-13-5/h1,6,9H,2-3,11H2,(H,17,18)(H,12,13,14)/t6-,9-/m0/s1

Upstream product

• 106134-67-2 (6R,7R)-trimethylsilyl 7-(trimethylsilyl)amino-3-iodomethylceph-3-em-4-carboxylate 
• 59032-27-8 sodium 1H-1,2,3-triazole-4-thiolate 
• 111389-99-2 (6R,7R)-Trimethylsilyl 7-[((Trimethylsilyl)oxy)carbonyl]-amino-3-iodomethylceph-3-em-4-carboxylate 
• 6440-06-8 5-mercapto-1H-1,2,3-triazole 
• 957-68-6 7-Aminocephalosporanic acid 
• 288-36-8 1,2,3-triazole 
• 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 

Relevant articles and documents

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.

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).

Cephalosporin intermediates

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, and intermediates in, the preparation of the above compounds; and processes for the preparation of broad-spectrum cephalosporin antibiotics.

Cephalosporin antibiotics

Novel cephalosporin antibiotic derivatives.

Trifluoromethylmercaptoacetamidocephalosporins

This invention is directed to antibacterial compounds, in particular, to 7-trifluoromethylmercaptoacetamidocephalosporins.