7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

Base Information

• Chemical Name: 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid
• CAS No.: 128454-32-0
• Molecular Formula: C₃₃H₂₇N₅O₅S₂
• Molecular Weight: 637.74
• Mol file: 128454-32-0.mol

Synonyms:7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

Chemical Property of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

There total 12 articles about 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-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:

7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid, p-toluenesulfonic acid, 2(N,N-dimethylacetamide) → 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid (128454-32-0)

Guidance literature:

With ammonium hydroxide; In methanol; at 25 - 30 ℃; pH=4.0 - 4.5;

Reference yield:

diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino]-3-vinyl-3-cephem-4-carboxylate (123201-39-8) → 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid (128454-32-0)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; In dichloromethane; at 0 - 5 ℃;

DOI:10.1016/S0014-827X(03)00063-6

Reference yield:

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) → 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid (128454-32-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N,O-bis(trimethylsilyl)acetamide / N,N-dimethyl-acetamide / 0.5 h / 20 °C

1.2: 51.9 percent / N,N-dimethyl-acetamide / 1.5 h / -20 - -10 °C

2.1: ethyl acetate / 1 h / 20 °C

3.1: PBr / tetrahydrofuran / 0.33 h / -5 °C

4.1: ethyl acetate / 5 h / 20 °C

5.1: 4.04 g / aq. Na₂CO₃ / CH₂Cl₂ / 1.5 h / 20 °C

6.1: PCl₅; pyridine / CH₂Cl₂ / 1.5 h / 8 - 10 °C

6.2: MeOH / CH₂Cl₂ / 1.25 h / -20 - -10 °C

6.3: 90 percent / H₂O / -50 °C

7.1: 92.4 percent / N,N-dimethylaniline; POCl₃ / CH₂Cl₂ / 1.5 h / -15 - -10 °C

8.1: TFA; anisole / CH₂Cl₂ / 0 - 5 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; phosphorus pentachloride; sodium carbonate; methoxybenzene; N,N-dimethyl-aniline; trifluoroacetic acid; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; ethyl acetate; 5.1: Wittig reaction;

DOI:10.1016/S0014-827X(03)00063-6

upstream raw materials:

diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino]-3-vinyl-3-cephem-4-carboxylate

(6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

diphenylmethyl 7β-phenylacetamido-3-vinyl-3-cephem-4-carboxylate

ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate

Downstream raw materials:

3-methyl cefdinir

Cefdinir sulfoxide

cefdinir

Refernces

• 1、 Gonzalez, Maritza,Rodriguez, Zalua,Tolon, Blanca,Rodriguez, Juan C.,Velez, Herman,Valdes, Barbara,Lopez, Miguel A.,Fini, Adamo. "An alternative procedure for preparation of cefdinir". . p. 409 - 418. Retrieved 2007/10/03.