7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-YL)thiomethyl]cephalosphoranic acid

Base Information

• Chemical Name: 7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-YL)thiomethyl]cephalosphoranic acid
• CAS No.: 30246-33-4
• Molecular Formula: C11H12N4O3S3
• Molecular Weight: 344.439
• European Community (EC) Number: 250-099-1
• Mol file: 30246-33-4.mol

Synonyms:7-AMINO-3-[(5-METHYL-1,3,4-THIADIAZOL-2-YL)THIOMETHYL]CEPHALOSPHORANIC ACID;30246-33-4;C11-H12-N4-O3-S3;SCHEMBL11675089;BCP12160;MFCD29913098;W-110774;(7R)-7-amino-3-((5-methyl-1,3,4-thiadiazol-2-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property of 7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-YL)thiomethyl]cephalosphoranic acid

Chemical Property:

• Vapor Pressure: 2.53E-19mmHg at 25°C
• Refractive Index: 1.768
• Boiling Point: 678.2 °C at 760 mmHg
• PKA: 2.52±0.50(Predicted)
• Flash Point: 364 °C
• PSA: 188.25000
• Density: 1.72 g/cm³
• LogP: 1.15790
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: CHCl3 (Slightly, Heated), DMF (Very Slightly), DMSO (Slightly)
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 344.00715378
• Heavy Atom Count: 21
• Complexity: 515

Purity/Quality:

99% ^*data from raw suppliers

7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-3-cephem-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)N)SC2)C(=O)O
• Isomeric SMILES: CC1=NN=C(S1)SCC2=C(N3C([C@@H](C3=O)N)SC2)C(=O)O
• Uses: 7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-3-cephem-4-carboxylic Acid is a substrate used in the assessment of immobilized PGA orientation and in the synthesis of beta lactam antibiotics.

Technology Process of 7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-YL)thiomethyl]cephalosphoranic acid

There total 13 articles about 7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-YL)thiomethyl]cephalosphoranic 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: 97.0%

7-phenylacetylamino-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (107447-96-1) → (6R,7R)-7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (30246-33-4)

Guidance literature:

7-phenylacetylamino-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester; With p-cresol; at 45 - 50 ℃; for 1h;

With penicillin G acylase; at 37 ℃; for 1h; Temperature; Enzymatic reaction;

Reference yield: 96.0%

2-mercapto-5-methyl-1,3,4-thiadiazole (29490-19-5) + 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid → 7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid (30246-33-4)

Guidance literature:

With boric acid; triethylamine; In water;

Reference yield: 95.0%

2-mercapto-5-methyl-1,3,4-thiadiazole (29490-19-5) + 7-Aminocephalosporanic acid (957-68-6) → (6R,7R)-7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (30246-33-4)

Guidance literature:

With boron trifluoride dimethyl carbonate complex; acetic acid; at 5 - 10 ℃; Temperature;

upstream raw materials:

2-mercapto-5-methyl-1,3,4-thiadiazole

3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0 ]oct-2-ene-2-carboxylic acid sodium salt

7-amino-3-<(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl>-Δ³-cephem-4-carboxylic acid hydrochloride

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

Downstream raw materials:

7-(phenylacetamido)-3-(((2-methyl-1,3,4-thiadiazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acid

(6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Refernces

• 1、 -. "Cefazedone synthesis method". Paragraph 0024-0032. . Retrieved 2019/12/25.
• 2、 -. "A head west spore alkone sodium synthetic method (by machine translation)". Paragraph 0034; 0035; 0038; 0039; 0042; 0043; 0046; 0047. . Retrieved 2019/04/26.