p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

Base Information

• Chemical Name: p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate
• CAS No.: 189507-47-9
• Molecular Formula: C₂₁H₂₀ClFN₆O₆S₂
• Molecular Weight: 571.01
• Mol file: 189507-47-9.mol

Synonyms:

Chemical Property of p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

There total 1 articles about p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-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:

2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid (116833-10-4) → p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (189507-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: PCl₅ / CH₂Cl₂ / 2.5 h / -15 °C

2: 85 percent / N,O-bis(trimethylsilyl)acetamide / CH₂Cl₂ / 1 h / -20 °C

With N,O-bis-(trimethylsilyl)-acetamide; phosphorus pentachloride; In dichloromethane;

DOI:10.1016/S0968-0896(00)00214-5

Reference yield:

p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (189507-47-9) → (6R,7R)-7-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-fluoromethoxyimino]-acetylamino}-3-iodomethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (768399-58-2)

Guidance literature:

With sodium iodide; In acetone; at 20 ℃; for 1.5h;

DOI:10.1016/S0968-0896(00)00214-5

Reference yield:

p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (189507-47-9) → Trifluoro-acetate6-[(6R,7R)-7-{2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-fluoromethoxyimino]-acetylamino}-2-(4-methoxy-benzyloxycarbonyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-imidazo[5,1-b]thiazol-6-ium;

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaI / acetone / 1.5 h / 20 °C

2.1: dimethylformamide / 20 °C

2.2: dimethylformamide; H₂O / 20 °C

With sodium iodide; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0968-0896(00)00214-5

upstream raw materials:

2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid

Downstream raw materials:

(6R,7R)-7-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-fluoromethoxyimino]-acetylamino}-3-iodomethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester