(6R,7R)-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetyl]amino}-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: (6R,7R)-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetyl]amino}-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 189345-04-8
• Molecular Formula: C22H20N8O5S4
• Molecular Weight: 0
• UNII: H36Z0FHR8K
• DSSTox Substance ID: DTXSID90172341
• Metabolomics Workbench ID: 65219
• ChEMBL ID: CHEMBL4594371
• Mol file: 189345-04-8.mol

Synonyms:ceftaroline;T 91825;T-91825;T91825

Chemical Property of (6R,7R)-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetyl]amino}-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 8
• Exact Mass: 604.04395046
• Heavy Atom Count: 39
• Complexity: 1040

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCON=C(C1=NSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)SC4=NC(=CS4)C5=CC=[N+](C=C5)C)C(=O)[O-]
• Isomeric SMILES: CCO/N=C(/C1=NSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)SC4=NC(=CS4)C5=CC=[N+](C=C5)C)C(=O)[O-]

Technology Process of (6R,7R)-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetyl]amino}-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 6 articles about (6R,7R)-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetyl]amino}-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 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: 62.0%

2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetyl chloride hydrochloride + 7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate (189345-52-6) → ceftaroline (189345-04-8)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 5 ℃; for 0.5h;

DOI:10.1016/S0968-0896(03)00126-3

Reference yield:

(7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester (123054-30-8) → ceftaroline (189345-04-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C

2.1: dimethylformamide / 16 h / 20 °C

3.1: phosphorus pentachloride; pyridine / CH₂Cl₂ / 1 h / 5 °C

3.2: MeOH / CH₂Cl₂ / 0.5 h / -20 °C

4.1: 8.28 g / TFA; anisole / CH₂Cl₂ / 1 h / 20 °C

5.1: 62 percent / NaHCO₃ / tetrahydrofuran; H₂O / 0.5 h / 5 °C

With pyridine; phosphorus pentachloride; sodium hydride; sodium hydrogencarbonate; methoxybenzene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00126-3

Reference yield:

[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol (77168-63-9) → ceftaroline (189345-04-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C

2.1: dimethylformamide / 16 h / 20 °C

3.1: phosphorus pentachloride; pyridine / CH₂Cl₂ / 1 h / 5 °C

3.2: MeOH / CH₂Cl₂ / 0.5 h / -20 °C

4.1: 8.28 g / TFA; anisole / CH₂Cl₂ / 1 h / 20 °C

5.1: 62 percent / NaHCO₃ / tetrahydrofuran; H₂O / 0.5 h / 5 °C

With pyridine; phosphorus pentachloride; sodium hydride; sodium hydrogencarbonate; methoxybenzene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00126-3

upstream raw materials:

7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate

(7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester

[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

p-methoxybenzyl 7β-phenylacetamido-3-[4-(4-pyridyl)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate

Refernces