sodium (2S,5R,6R)-6-({[1-(4-bromophenyl)cyclopentyl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Base Information

• Chemical Name: sodium (2S,5R,6R)-6-({[1-(4-bromophenyl)cyclopentyl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 143407-71-0
• Molecular Formula: C20H23 Br N2 O4 S . Na
• Molecular Weight: 489.3584
• Mol file: 143407-71-0.mol

Synonyms:

Chemical Property of sodium (2S,5R,6R)-6-({[1-(4-bromophenyl)cyclopentyl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

• Vapor Pressure: 3.48E-21mmHg at 25°C
• Boiling Point: 710.5°C at 760 mmHg
• Flash Point: 383.5°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of sodium (2S,5R,6R)-6-({[1-(4-bromophenyl)cyclopentyl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

There total 5 articles about sodium (2S,5R,6R)-6-({[1-(4-bromophenyl)cyclopentyl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-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: 68.2%

6-Aminopenicillanic Acid (551-16-6) + 1-(4-bromophenyl)cyclopentane-1-carboxylic acid chloride (143328-29-4) → Sodium; (2S,5R,6R)-6-{[1-(4-bromo-phenyl)-cyclopentanecarbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (143407-71-0)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 0 - 20 ℃; for 6h;

DOI:10.1007/BF00766460

Reference yield:

4-Bromophenylacetonitrile (16532-79-9) → Sodium; (2S,5R,6R)-6-{[1-(4-bromo-phenyl)-cyclopentanecarbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (143407-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaOH / 1.) 45 deg C, 2.) 120 deg C, 12 h

2: 60.4 percent / KOH / various solvent(s) / 12 h / Heating

3: 1.) triethylamine, chlorocarbonic acid ethyl ester, 2.) NaHCO₃ / 1.) acetone, from 0 deg C, 30 min, to RT, 2 h, 2.) acetone, water, 4 h

With potassium hydroxide; sodium hydroxide; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; In various solvent(s);

DOI:10.1007/BF00766460

Reference yield:

1-(4-bromophenyl)cyclopentane-1-carbonitrile (143328-19-2) → Sodium; (2S,5R,6R)-6-{[1-(4-bromo-phenyl)-cyclopentanecarbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (143407-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 60.4 percent / KOH / various solvent(s) / 12 h / Heating

2: 1.) triethylamine, chlorocarbonic acid ethyl ester, 2.) NaHCO₃ / 1.) acetone, from 0 deg C, 30 min, to RT, 2 h, 2.) acetone, water, 4 h

With potassium hydroxide; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; In various solvent(s);

DOI:10.1007/BF00766460

upstream raw materials:

6-Aminopenicillanic Acid

1-(4-bromophenyl)cyclopentanecarboxylic acid

1-(4-bromophenyl)cyclopentane-1-carboxylic acid chloride

4-Bromophenylacetonitrile

Refernces