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

Base Information

• Chemical Name: (6R,7R)-7-[(2,5-dichlorophenyl)thiomethylcarbonylamino]-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 181375-17-7
• Molecular Formula: C₁₆H₁₃Cl₃N₂O₄S₂
• Molecular Weight: 467.781
• Mol file: 181375-17-7.mol

Synonyms:(6R,7R)-7-[(2,5-dichlorophenyl)thiomethylcarbonylamino]-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property of (6R,7R)-7-[(2,5-dichlorophenyl)thiomethylcarbonylamino]-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-7-[(2,5-dichlorophenyl)thiomethylcarbonylamino]-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 6 articles about (6R,7R)-7-[(2,5-dichlorophenyl)thiomethylcarbonylamino]-3-chloromethyl-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: 93.8%

(6-R-trans)-3-(chloromethyl)-7-[[[(2,5-dichlorophenyl)thio]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester (181375-13-3) → (6R,7R)-7-[(2,5-dichlorophenyl)thiomethylcarbonylamino]-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (181375-17-7)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.666667h;

DOI:10.1016/S0040-4020(00)00418-X

Reference yield:

[(2,5-dichlorophenyl)thio]acetic acid (6274-27-7) → (6R,7R)-7-[(2,5-dichlorophenyl)thiomethylcarbonylamino]-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (181375-17-7)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 2 h / -25 °C

2: 88 percent / N-methylmorpholine / CH₂Cl₂ / 0.67 h / -25 °C

3: 93.8 percent / TFA; anisole / CH₂Cl₂ / 0.67 h / 0 °C

With 4-methyl-morpholine; oxalyl dichloride; methoxybenzene; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Acylation / 3: Substitution;

DOI:10.1016/S0040-4020(00)00418-X

Reference yield:

2,5-dichlorbenzenethiol (5858-18-4) → (6R,7R)-7-[(2,5-dichlorophenyl)thiomethylcarbonylamino]-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (181375-17-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / aq. NaOH / 1 h / 100 °C

2: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 2 h / -25 °C

3: 88 percent / N-methylmorpholine / CH₂Cl₂ / 0.67 h / -25 °C

4: 93.8 percent / TFA; anisole / CH₂Cl₂ / 0.67 h / 0 °C

With 4-methyl-morpholine; sodium hydroxide; oxalyl dichloride; methoxybenzene; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution / 3: Acylation / 4: Substitution;

DOI:10.1016/S0040-4020(00)00418-X

upstream raw materials:

(6-R-trans)-3-(chloromethyl)-7-[[[(2,5-dichlorophenyl)thio]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester

(2,5-Dichloro-phenylsulfanyl)-acetyl chloride

[(2,5-dichlorophenyl)thio]acetic acid

2,5-dichlorbenzenethiol