(4-Nitrophenyl)methyl 3-{[5-(dimethylcarbamoyl)-1-{[(4-nitrophenyl)methoxy]carbonyl}pyrrolidin-2-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Base Information

• Chemical Name: (4-Nitrophenyl)methyl 3-{[5-(dimethylcarbamoyl)-1-{[(4-nitrophenyl)methoxy]carbonyl}pyrrolidin-2-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS No.: 96036-02-1
• Molecular Formula: C32H35N5O11S
• Molecular Weight: 697.723
• DSSTox Substance ID: DTXSID40694109
• Mol file: 96036-02-1.mol

Synonyms:DTXSID40694109;A845536;(4-nitrophenyl)methyl 3-[5-(dimethylcarbamoyl)-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-2-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxidanylidene-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;(4-nitrophenyl)methyl 3-{[5-(dimethylcarbamoyl)-1-{[(4-nitrophenyl)methoxy]carbonyl}pyrrolidin-2-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;3-[[5-[dimethylamino(oxo)methyl]-1-[(4-nitrophenyl)methoxy-oxomethyl]-2-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

Chemical Property of (4-Nitrophenyl)methyl 3-{[5-(dimethylcarbamoyl)-1-{[(4-nitrophenyl)methoxy]carbonyl}pyrrolidin-2-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical Property:

• Vapor Pressure: 6.99E-35mmHg at 25°C
• Melting Point: 150-153°C (dec.)
• Refractive Index: 1.672
• Boiling Point: 900.3 °C at 760 mmHg
• PKA: 14.36±0.20(Predicted)
• Flash Point: 498.3 °C
• PSA: 233.63000
• Density: 1.49 g/cm³
• LogP: 4.13860
• Storage Temp.: 2-8°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 697.20537812
• Heavy Atom Count: 49
• Complexity: 1350

Purity/Quality:

99% ^*data from raw suppliers

ProtectedMeropenem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(C(=O)N2C(=C1SC3CCC(N3C(=O)OCC4=CC=C(C=C4)[N+](=O)[O-])C(=O)N(C)C)C(=O)OCC5=CC=C(C=C5)[N+](=O)[O-])C(C)O
• Uses: Protected meropenem (CAS# 96036-02-1) is a derivative of meropenem (M225668), an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections, including meningitis and pneumonia.

Technology Process of (4-Nitrophenyl)methyl 3-{[5-(dimethylcarbamoyl)-1-{[(4-nitrophenyl)methoxy]carbonyl}pyrrolidin-2-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 32 articles about (4-Nitrophenyl)methyl 3-{[5-(dimethylcarbamoyl)-1-{[(4-nitrophenyl)methoxy]carbonyl}pyrrolidin-2-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-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: 91.3%

(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) → p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (96036-02-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -15 - -10 ℃; for 5 - 8h;

Reference yield: 89.0%

p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (105344-45-4) → p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (96036-02-1)

Guidance literature:

With phosphate buffer pH 3; for 2.5h; Ambient temperature;

DOI:10.1248/cpb.42.1381

Reference yield: 84.0%

citric acid monohydrate (5949-29-1) + p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (105344-45-4) → p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (96036-02-1)

Guidance literature:

In methanol;

upstream raw materials:

p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

(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

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

Downstream raw materials:

meropenem

Refernces

• 1、 -. "IMPROVED METHOD FOR PREPARING MEROPENEM USING ZINC POWDER". Page/Page column 7. . Retrieved 2012/02/04.
• 2、 -. "Improved process for the preparation of carbapenem using carbapenem intermediates and recovery of carbapenem". . . Retrieved 2011/12/03.