5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-7-[(phenylacetyl)amino]-, (4-methoxyphenyl)methyl ester, (6R,7R)-

Base Information

• Chemical Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-7-[(phenylacetyl)amino]-, (4-methoxyphenyl)methyl ester, (6R,7R)-
• CAS No.: 138514-31-5
• Molecular Formula: C29H27N3O5S2
• Molecular Weight: 561.682
• Mol file: 138514-31-5.mol

Synonyms:

Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-7-[(phenylacetyl)amino]-, (4-methoxyphenyl)methyl ester, (6R,7R)-

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-7-[(phenylacetyl)amino]-, (4-methoxyphenyl)methyl ester, (6R,7R)-

There total 4 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-7-[(phenylacetyl)amino]-, (4-methoxyphenyl)methyl ester, (6R,7R)- 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: 96.2%

4-methyl-1,3-thiazole-5-carbaldehyde (82294-70-0) + (6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (104146-10-3) → 7-phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)ethenyl]-4-aminocephalosporanic acid p-methoxybenzylester (138514-31-5)

Guidance literature:

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester; With triphenylphosphine; sodium iodide; In water; ethyl acetate; at 30 ℃; for 1.5h; Large scale;

4-methyl-1,3-thiazole-5-carbaldehyde; In water; ethyl acetate; at -25 ℃; pH=7; Solvent; Large scale;

Reference yield: 93.7%

4-methyl-1,3-thiazole-5-carbaldehyde (82294-70-0) + [(6R,7R)-2-(4-Methoxy-benzyloxycarbonyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-triphenyl-phosphonium; iodide (119636-62-3) → 7-phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)ethenyl]-4-aminocephalosporanic acid p-methoxybenzylester (138514-31-5)

Guidance literature:

With sodium D-gluconate; at -15 - 3 ℃; for 6h; Temperature;

Reference yield:

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (104146-10-3) → 7-phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)ethenyl]-4-aminocephalosporanic acid p-methoxybenzylester (138514-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaI / acetone / 2 h / Ambient temperature

2: NaHCO₃ / CH₂Cl₂; H₂O / 17 h / Ambient temperature

With sodium hydrogencarbonate; sodium iodide; In dichloromethane; water; acetone;

DOI:10.1248/cpb.39.2433

upstream raw materials:

4-methyl-1,3-thiazole-5-carbaldehyde

[(6R,7R)-2-(4-Methoxy-benzyloxycarbonyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-triphenyl-phosphonium; iodide

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Downstream raw materials:

p-Methoxybenzyl 7-amino-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate

cefditoren pivoxil

p-Methoxybenzyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate

7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt