(6R-trans)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

Base Information

• Chemical Name: (6R-trans)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
• CAS No.: 79350-10-0
• Molecular Formula: C₁₄H₁₄N₄O₄S₂
• Molecular Weight: 366.422
• Hs Code.: 2934990002
• UNII: VPE6YB7J69
• ChEMBL ID: CHEMBL60169
• Mol file: 79350-10-0.mol

Synonyms:79350-10-0;(6R-trans)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;(6R,7R)-7-(2-(2-aminothiazol-4-yl)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-7-[[2-(2-Amino-1,3-thiazol-4-yl)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;VPE6YB7J69;CHEMBL60169;SCHEMBL5323243;(6R,7R)-7-[2-(2-AMINO-1,3-THIAZOL-4-YL)ACETAMIDO]-3-ETHENYL-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2-amino-4-thiazolyl)acetyl]amino]-3-ethenyl-8-oxo-, (6R-trans)-;7-(2-(2-imino-2,3-dihydrothiazol-4-yl)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-

Chemical Property of (6R-trans)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

Chemical Property:

• Melting Point: >220°C (dec.)
• Boiling Point: 840.7±65.0 °C(Predicted)
• PKA: 2.81±0.50(Predicted)
• Density: 1.62±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 366.04564729
• Heavy Atom Count: 24
• Complexity: 638

Purity/Quality:

95-99% ^*data from raw suppliers

(6R-trans)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1=C(N2C(C(C2=O)NC(=O)CC3=CSC(=N3)N)SC1)C(=O)O
• Isomeric SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC3=CSC(=N3)N)SC1)C(=O)O
• Uses: (6R-trans)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, is the impurity of Cefdinir (C242670), a Cephalosporin antibiotic structurally similar to Cefixime. It can be used to treat infections caused by several Gram-negative and Gram-positive bacteria.

Technology Process of (6R-trans)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

There total 6 articles about (6R-trans)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-ethenyl-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:

[2-[(triphenyl-methyl)-amino]-thiazol-4-yl] acetic acid (64220-26-4) → 7-[(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (79350-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl chloride / diethyl ether; dimethylformamide; CH₂Cl₂ / 0.08 h / -10 °C

2: pyridine; dimethylformamide / 0.5 h / -10 - -5 °C

3: dimethylformamide; CH₂Cl₂; H₂O; pyridine / 15 h

4: 98percent formic acid / 2 h / Ambient temperature

With formic acid; oxalyl dichloride; In pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00118a022

Reference yield:

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (79349-82-9) → 7-[(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (79350-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1: dimethylformamide / Ambient temperature

2: pyridine; dimethylformamide / 0.5 h / -10 - -5 °C

3: dimethylformamide; CH₂Cl₂; H₂O; pyridine / 15 h

4: 98percent formic acid / 2 h / Ambient temperature

With formic acid; In pyridine; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00118a022

Reference yield:

C12H18N2O3SSi → 7-[(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (79350-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; dimethylformamide / 0.5 h / -10 - -5 °C

2: dimethylformamide; CH₂Cl₂; H₂O; pyridine / 15 h

3: 98percent formic acid / 2 h / Ambient temperature

With formic acid; In pyridine; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00118a022

upstream raw materials:

[2-[(triphenyl-methyl)-amino]-thiazol-4-yl] acetic acid

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

<2-(tritylamino)thiazol-4-yl>acetyl chloride

Refernces