96034-57-0

Basic information

• Product Name: TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE
• Synonyms: TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE;P-NITRO BENZYL 2(S) CARBOXY TRANS 4(R) HYDROXY L P;(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic Acid 1-(4-Nitrobenzyl) Ester;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-[(4-nitrophenyl)Methyl] ester;(2S,4R)-1-(4-Nitrobenzyloxycarbonyl)-4-hydroxyproline;1,2-Pyrrolidinedicarboxylicacid, 4-hydroxy-, 1-[(4-nitrophenyl)methyl] ester, (2S,4R)-;(2S,4R)-1-((4-NITROBENZYLOXY)CARBONYL)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS NO: 96034-57-0
• Molecular Formula: C₁₃H₁₄N₂O₇
• Molecular Weight: 310.25900
• EINECS: 1533716-785-6
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 96034-57-0.mol

Chemical Properties

• Melting Point: 182-183℃
• Boiling Point: 578.308 °C at 760 mmHg
• Flash Point: 303.55 °C
• Appearance: /Solid
• Density: 1.557
• Storage Temp.: Refrigerator
• Solubility: Dichloromethane (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol
• PKA: 3.69±0.40(Predicted)
• CAS DataBase Reference: TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE(96034-57-0)
• EPA Substance Registry System: TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE(96034-57-0)

Safety Data

• Hazardous Substances Data: 96034-57-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the production of Meropenem.

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 4457-32-3 4-nitrobenzyl chloroformate 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 132984-58-8 trans-4-chloroacetoxy-1-(4-nitro-benzyloxycarbonyl)-L-proline 
• 188578-74-7 (2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-4-hydroxyprolinanilide 
• 101803-29-6 (2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 
• 138324-82-0 (2S,4R)-4-mesyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid methyl ester 
• 96035-08-4 (2S,4R)-2-carbamoyl-4-mesyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine 
• 230964-57-5 p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate 
• 188578-76-9 2-Phenyl-2,5-diazabicyclo[2.2.1]heptan-3-one 
• 188578-75-8 2-Phenyl-5-(p-nitrobenzyloxycarbonyl)-2,5-diazabicyclo[2.2.1]heptan-3-one 
• 188578-77-0 (2S,4R)-N-Benzyl-4-hydroxy-1-(p-nitrobenzyloxycarbonyl)prolinamide 

Relevant articles and documents

DERIVATIZATION OF BETA-LACTAM ANTIBIOTICS AS CALIBRATORS/ISTD IN MASSSPEC MEASUREMENTS

The invention relates to a complex comprising an antibiotic substance and a nucleophilic derivatization reagent, compositions comprising the complex, kits comprising complex or composition, as well as uses of the complex or composition.

Meropenem side chain intermediate and method for preparing same

The invention relates to a meropenem side chain intermediate and a method for preparing the same, and belongs to the technical field of medicinal chemistry. The meropenem side chain intermediate and the method have the advantages that the requirements of

A luer Ertapenem, luer he lateral chain and its preparation method

The invention discloses ertapenem and ertapenem side chains, as well as preparation methods of ertapenem and ertapenem side chains. L-hydroxyproline is protected by p-nitrobenzyl ester to obtain (2S,4R)-4-hydroxyl-1-(((4-Nitrobenzformyl)-oxyl)caboyl)pyrrolidine-2-carboxylic acid; then 4-nitro(1S,4S)-3-oxo-2-thia-5-azabicyclo[2.2.1]heptan-5-carboxylic anhydride can be obtained, and reacts with m-aminobenzoic acid p-nitrobenzyl ester to obtain ertapenem side chain III; and the ertapenem can be synthesized through two-step chemical reaction of condensation and deprotection to the ertapenem side chain III and a raw material MAP. An ertapenem side chain I (10), an ertapenem side chain II (13) and the ertapenem side chain III (2) which are prevailing in the market can be synthesized through simple steps, without the need of ultralow temperature, industrialization is easy, and the product purity is high, and the operation is simple and convenient.

Selective Inhibition of an Apicoplastic Aminoacyl-tRNA Synthetase from Plasmodium falciparum

The resistance of malaria parasites to available drugs continues to grow, and this makes the need for new antimalarial therapies pressing. Aminoacyl-tRNA synthetases (ARSs) are essential enzymes and well-established antibacterial targets and so constitute

AN IMPROVED PROCESS FOR THE PREPARATION OF MEROPENEM

The present invention provides an improved process for the preparation of methyl carbapenem derivative of formula (I) or its pharmaceutically acceptable salts or hydrates thereof in a pure form.

A PROCESS FOR THE PREPARATION OF THE INTERMEDIATE OF Β-METHYL CARBAPENEM

A process of preparation of the intermediate of β-methyl carbapenem is disclosed, in which 4-acetylazacyclobutanone as the raw material is firstly reacted with α-bromopropionamide having a big inductive group. Since this reaction is highly stereoselectivity, most of the product is the required parent nucleus of β-methyl carbapenem, a product of β-configuration. Compared with the prior art, the process of the present invention is highly-yielding, cost-effective and can be used for large scale production.

A PROCESS FOR THE PREPARATION OF MEROPENEM

The invention relates to a process for the preparation of meropenem, a β-methylcarbopenem. The said process comprises the following steps: preparing the compound of Formula (XI) from the compound of Formula (IV) through three steps "one-pot process"; then condensing the compound of Formula (XI) with the compound of Formula (XX) to form the compound of Formula (XXIV); finally preparing meropenam of Formula (I) from the compound of Formula (XXIV) by deprotection reaction by means of catalyst. The process of the invention is easily to carry out, the product is isolated in high content and yield, and the cost is reduced, thereby overcoming the shortage of the prior art.

Practical large-scale synthesis of the 2-aminomethylpyrrolidin-4-ylthio-containing side chain of the novel carbapenem antibiotic doripenem

The first synthesis using an original procedure and a practical large-scale process using an improved procedure for the synthesis of the N-PNZ-protected 2-aminomethylpyrrolidin-4-ylthio-containing side chain of doripenem hydrate (S-4661), a novel parenteral 1β-methylcarbapenem antibiotic, are described, trans-4-Hydroxy-L-proline (4) was converted in an efficient process to (2S,4S)-4-acetylthio-2-(N-sulfamoyl-tert-butoxycarbonylaminomethyl) -1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3) in 55-56% overall yield via a six-step sequence, which includes the two alternative routes to intermediate 13. This process requires no chromatographic purifications, no cryogenic temperatures, no haloalkane solvents, and short operating times and is amenable to a multikilogram-scale preparation. Several kilograms of the side chain 3 were successfully prepared by this process.

Synthesis and antibacterial activity of new carbapenems containing isoxazole moiety

The synthesis and biological activity of a series of new 1β- methylcarbapenems 1a-g containing 5'-isoxazolopyrrolidin-3'-ylthio derivatives as C-2 side chain are described. Most compounds exhibited potent and well-balanced antibacterial activity as well as high stability to DHP-I comparable to that of meropenem. 1e and 1c showed the best combination of antibacterial activity and stability to DHP-I, respectively.

Synthesis and antibacterial activity of 1β-methylcarbapenem having a 1,3-diazabicyclo[3.3.0]octan-4-one moiety, Part II

The synthesis of a new series of 1β-methylcarbapenems having a 1,3- diazabicyclo[3.3.0]octan-4-one moiety is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria are tested and the effect of substituent on the bicyclic ring was investigated. A particular compound (11h) having aminoethyl group showed the most potent antibacterial activity.