7-Amino-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: 7-Amino-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 58909-56-1
• Molecular Formula: C12H13 N5 O5 S2
• Molecular Weight: 371.398
• DSSTox Substance ID: DTXSID20974411
• Mol file: 58909-56-1.mol

Synonyms:DTXSID20974411;7-amino-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property of 7-Amino-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• Boiling Point: 718℃[at 101 325 Pa]
• PKA: 2.49±0.50(Predicted)
• PSA: 202.24000
• Density: 2.03g/cm³
• LogP: -0.80770
• Water Solubility.: 200mg/L at 20℃
• XLogP3: -3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 371.03581088
• Heavy Atom Count: 24
• Complexity: 721

Purity/Quality:

99.9% ^*data from raw suppliers

7-Amino-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)thio]methyl]cephalosporanic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=NC(=O)C(=O)N1)SCC2=C(N3C(C(C3=O)N)SC2)C(=O)O
• Isomeric SMILES: CN1C(=NC(=O)C(=O)N1)SCC2=C(N3C([C@@H](C3=O)N)SC2)C(=O)O
• Uses: An intermediate in the synthesis of cephalosporin antibiotics, Ceftriaxone (C245000) and Cefixime (C242800).

Technology Process of 7-Amino-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 5 articles about 7-Amino-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-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: 95.1%

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine (58909-39-0) + 7-Aminocephalosporanic acid (957-68-6) → 7-aminoceftrizine (58909-56-1)

Guidance literature:

With boron trifluoride dimethyl carbonate complex; methanesulfonic acid; at 10 - 12 ℃; for 0.383333h; Reagent/catalyst;

Reference yield: 95.0%

7-Aminocephalosporanic acid (957-68-6) + 2,6-dimethyl-5-oxo-1,2,4-triazine-3-thiol → 7-amino-3-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazine-3-mercapto)methyl]-3 cephalosporin-4-carboxylic acid (58909-56-1)

Guidance literature:

With titanium tetrachloride; tetrabutyl titanium; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 5 ℃; for 4h;

Reference yield: 92.0%

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine (58909-39-0) + 7-Aminocephalosporanic acid (957-68-6) → 7-amino-3-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazine-3-mercapto)methyl]-3 cephalosporin-4-carboxylic acid (58909-56-1)

Guidance literature:

With aluminum (III) chloride; boron trifluoride; carbonic acid dimethyl ester; at 5 - 30 ℃; for 1h;

upstream raw materials:

7-Aminocephalosporanic acid

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

Downstream raw materials:

ceftriaxone disodium

(6R,7R)-7-<2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido>-3-<<(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid disodium salt (Z isomer)

ceftriaxone

2-Mercaptobenzothiazole

Refernces

• 1、 -. "A novel indication of a Rocephin (ceftriaxone sodium) pharmaceutical preparation for treating bacterial intimitis". Paragraph 0120-0121; 0126-0127; 0150-0153. . Retrieved 2019/11/13.
• 2、 -. "A synthesis method of Ceftriaxone sodium". Paragraph 0021-0022; 0036-0037. . Retrieved 2017/05/11.