(6R,7R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (6R,7R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 37539-03-0
• Molecular Formula: C10H11N5O3S2
• Molecular Weight: 313.361
• European Community (EC) Number: 253-547-4
• Mol file: 37539-03-0.mol

Synonyms:37539-03-0;(6R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-TACA;SCHEMBL8497460;MLOZJRLUNNFSGD-IOJJLOCKSA-N;BCP07332;7-amino-3 (1H-1,2,3-triazol-4-yl)thiomethylceph-3-em-4-carboxylic acid;7-amino-3-(1,2,3-triazol-5-yl-thiomethyl)-3-cephem-4-carboxylic acid;7-Amino-3-(1,2,3-triazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid;7-amino-3-(1H-1,2,3-triazol-4-yl)thiomethylceph-3-em-4-carboxylic acid;7-amino-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid;7-Amino-3-(1H-1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid;7-Amino-3-[S-(1,2,3-triazole-5-yl)-thiomethyl]3-cephem-4-carboxylic acid

Chemical Property of (6R,7R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 5.85E-22mmHg at 25°C
• Refractive Index: 1.798
• Boiling Point: 723.3 °C at 760 mmHg
• PKA: 2.56±0.50(Predicted)
• Flash Point: 391.2 °C
• PSA: 175.80000
• Density: 1.8g/cm³
• LogP: 0.11610
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly, Heated, Sonicated), Water (Slightly)
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 313.03033158
• Heavy Atom Count: 20
• Complexity: 486

Purity/Quality:

99% ^*data from raw suppliers

TACA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=C(N2C(S1)C(C2=O)N)C(=O)O)CSC3=NNN=C3
• Isomeric SMILES: C1C(=C(N2[C@H](S1)C(C2=O)N)C(=O)O)CSC3=NNN=C3
• Uses: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid is used in the preparation of triazole-based semi-synthetic cephalosporins.

Technology Process of (6R,7R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 10 articles about (6R,7R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

5-mercapto-1H-1,2,3-triazole (6440-06-8) + 7-Aminocephalosporanic acid (957-68-6) → (6R)-7t-amino-8-oxo-3-(1H-[1,2,3]triazol-4-ylsulfanylmethyl)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (37539-03-0)

Guidance literature:

With boron trifluoride; In acetonitrile; at 30 ℃; for 1.5h;

DOI:10.1248/cpb.33.5534

Reference yield:

→ 7-amino-3-[((1H-1,2,3-triazol-5-yl)thio)methyl]ceph-3-em-4-carboxylic acid (37539-03-0)

Guidance literature:

5-Amino-1.2.3-thiadiazol, NaOH, 7-Amino-cephalosporinsaeure;

Reference yield:

1,2,3-triazole (288-36-8) + (6R,7R)-trimethylsilyl 7-(trimethylsilyl)amino-3-iodomethylceph-3-em-4-carboxylate + sodium 1H-1,2,3-triazole-4-thiolate (59032-27-8) → 3-<(1H-1,2,3-triazol-4-ylthio)methyl>cephem (37539-03-0)

Guidance literature:

With pyridine; In dichloromethane; Chlorodifluoromethane;

upstream raw materials:

(6R,7R)-trimethylsilyl 7-(trimethylsilyl)amino-3-iodomethylceph-3-em-4-carboxylate

sodium 1H-1,2,3-triazole-4-thiolate

(6R,7R)-Trimethylsilyl 7-[((Trimethylsilyl)oxy)carbonyl]-amino-3-iodomethylceph-3-em-4-carboxylate

(6R,7R)-Trimethylsilyl 7-[((Trimethylsilyl)oxy)carbonyl]-amino-3-acetoxymethylceph-3-em-4-carboxylate

Refernces

• 1、 Walker, Donald G.,Brodfuehrer, Paul R.,Brundidge, Steven P.,Shih, Kun Mao,Sapino, Chester. "Use of Bistrimethylsilylated Intermediates in the Preparation of Semisynthetic 7-Amino-3-substituted-cephems. Expedient Syntheses of a New 3-cephalosporin". . p. 983 - 991. Retrieved 2007/10/02.
• 2、 Saikawa,Takano,Momonoi,et al.. "An efficient method for the preparation of 3-(substituted thiomethyl)-7-aminocephalosporins". . p. 5534 - 5538. Retrieved 2007/10/02.