(4R,5S,6S)-3-[[(3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (4R,5S,6S)-3-[[(3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS No.: 119478-56-7
• Molecular Formula: C₁₇H₂₅N₃O₅S*3H₂O
• Molecular Weight: 437.514
• Hs Code.: 2941906000
• Mol file: 119478-56-7.mol

Synonyms:Meropenem trihydrate;meropenem;meropenemtrihydrate(3-[[5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylicacidtrihydrate);3-[[5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylic acid trihydrate;(4r,5s,6s)-3-[[(3s,5s)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;(4r,5s,6s)-3-[[(3s,5s)-5-(dimethylcarbamoyl)-3-pyrrolidinyl]thio]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid trihydrate;eropenem trihydrate;meropenem trihydrochlorid e;

Chemical Property of (4R,5S,6S)-3-[[(3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.27E-18mmHg at 25°C
• Refractive Index: 1.639
• Boiling Point: 627.4 °C at 760 mmHg
• Flash Point: 333.2 °C
• PSA: 163.17000
• Density: 1.42 g/cm³
• LogP: -0.23420
• Storage Temp.: ?20°C
• Solubility.: Soluble in aqueous solution at approximately 5mg/ml

Purity/Quality:

Meropenem Trihydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Meropenem trihydrate is a carbapenem antibiotic with wide spectrum of antibacterial. It is an ultra-broad spectrum beta-lactam antibiotic and has antibacterial activity against Gram-negative and Gram-positive bacteria as well as anaerobic microorganisms such as Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, Enterobacter species, Serratia marcescens, Streptococcus pyogenes, Streptococcus agalactiae and Citrobacter sp. Meropenem trihydrate is indicated for the treatment of serious bacterial infection including complicated skin infections, complicated intra-abdominal infections, urinary tract infections, severe pneumonia, broncho-pulmonary infections and bacterial meningitis.
• Clinical Use: Meropenem is a second-generation carbapenem that, todate, has undergone the most extensive clinical evaluation.It has recently been approved as Merrem for the treatmentof infections caused by multiply-resistant bacteria and forempirical therapy for serious infections, such as bacterialmeningitis, septicemia, pneumonia, and peritonitis.Meropenem exhibits greater potency against Gram-negativeand anaerobic bacteria than does imipenem, but it is slightlyless active against most Gram-positive species. It is not effectiveagainst MRSA. Meropenem is not hydrolyzed byDHP-I and is resistant to most β-lactamases, including a fewcarbapenemases that hydrolyze carbapenem.
• Indications: Intra-abdominal infectionsBacterial meningitis (pediatric patients >3 months)Complicated skin and skin structure infections
• Drug interactions: Potentially hazardous interactions with other drugs Antiepileptics: concentration of valproate reduced - avoid. Probenecid: avoid concomitant use

Technology Process of (4R,5S,6S)-3-[[(3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

There total 3 articles about (4R,5S,6S)-3-[[(3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-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: 97.8%

C32H33N5O12S → meropenem trihydrate (119478-56-7)

Guidance literature:

With 3,5-Lutidine; palladium 10% on activated carbon; water; hydrogen; In tetrahydrofuran; at 20 ℃; for 6h; Autoclave; Large scale;

Reference yield:

meropenem (96036-03-2) → meropenem trihydrate (119478-56-7)

Guidance literature:

With water; In tetrahydrofuran; at 5 - 10 ℃; for 5h; Product distribution / selectivity;

Reference yield:

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (93711-81-0,90776-59-3,189188-38-3) + (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine (96034-64-9) → meropenem trihydrate (119478-56-7)

Guidance literature:

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine; In N,N-dimethyl-formamide; at -50 - 20 ℃; for 1h;

With 4-methyl-morpholine; hydrogen; acetic acid; 5%-palladium/activated carbon; In ethyl acetate; at 20 - 25 ℃; for 3h; pH=~ 7; Product distribution / selectivity; Aqueous buffer;

upstream raw materials:

meropenem

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Refernces

• 1、 -. "IMPROVED PROCESS FOR PRODUCING CARBAPENEM COMPOUND". Page/Page column 12. . Retrieved 2009/01/24.