144542-43-8

Basic information

• Product Name: 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)
• Synonyms: 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI);(R)-2-Oxo-4-oxazolidinecarboxylic acid methyl ester;(R)-Methyl 2-oxooxazolidine-4-carboxylate;4-Oxazolidinecarboxylic acid, 2-oxo-, Methyl ester, (R)-;(4R)-(9CI);R-2-Oxo-4-oxazolidinecarboxylic acid;4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-;methyl (R)-2-oxooxazolidine-4-carboxylate
• CAS NO: 144542-43-8
• Molecular Formula: C₅H₇NO₄
• Molecular Weight: 145.12
• Product Categories: CARBOXYLICESTER
• Mol File: 144542-43-8.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 357.8±31.0 °C(Predicted)
• Appearance: /
• Density: 1.320
• Storage Temp.: 2-8°C
• PKA: 10.82±0.40(Predicted)
• CAS DataBase Reference: 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)(144542-43-8)
• EPA Substance Registry System: 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)(144542-43-8)

Safety Data

• Hazardous Substances Data: 144542-43-8(Hazardous Substances Data)

Usage

General Description

4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) is a chemical compound, also known by the name "Methylester; 4-Oxazolidinecarboxylic acid". As its name suggests, it is a derivative of oxazolidine, which is a five-member heterocyclic compound containing an oxygen atom, a nitrogen atom, and three carbon atoms in the ring structure. As a methylester, it has undergone an esterification process, which replaces a hydrogen atom in the acid group with a methyl group. The (4R)-(9CI) determines the specific spatial arrangement of the compound, with the 'R' referring to its rectus chirality (the arrangement of its atoms in space) and '9CI' is an index term helping in identifying or categorizing the compound. More information like its molecular weight, solubility, and other physical and chemical properties needs further research or scientific analysis.

Upstream product

• 67-56-1 methanol 
• 56-45-1 L-serin 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 19525-95-2 (S)-2-oxo-oxazolidine-4-carboxylic acid 
• 75-44-5 phosgene 
• 2788-84-3 (S)-serine methyl ester 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 584-08-7 potassium carbonate 
• 5874-57-7 R-(-)-serine methyl ester hydrochloride 
• 2104-89-4 D-serine methyl ester 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 74124-79-1 di(succinimido) carbonate 
• 120-72-9 indole 
• 126496-79-5 (S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester 

Downstream Products

• 928112-68-9 methyl (4S)-3-[(4-methoxyphenyl)methyl]-2-oxo-1,3-oxazolidine-4-carboxylate 
• 173604-32-5 (S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one 
• 144542-44-9 (4S)-4-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 264621-76-3 methyl (4S)-3-but-3-enyl-2-oxooxazolidine-4-carboxylate 
• 264621-78-5 but-3-enyl (4S)-3-but-3-enyl-2-oxooxazolidine-4-carboxylate 
• 132682-23-6 (4R)-4-(hydroxymethyl)-1,3-oxazolidin-2-one 

Relevant articles and documents

Synthesis of conformationally restricted analogs of kainic acid. Is the conformation of the C4-substituent of kainoid important to its neuroexcitatory activity?

Conformationally restricted analogs of kainic acid, which have an azabicyclo[3.3.0]octane system, were synthesized through the intramolecular addition reaction of trimethylenemethane to the α,β-unsaturated ester. Every synthesized isomer showed very weak depolarizing activity. These results indicate that the plane of the isopropenyl group of kainic acid should be diagonal to the pyrrolidine ring to show potent activity.

Total syntheses of isodomoic acids G and H: An exercise in tetrasubstituted alkene synthesis

A unified approach to the pyrrolidine triacid natural products isodomoic acids G and H has been developed. Total syntheses of both natural products were completed, and determination of the correct stereostructure of isodomoic acid G was established by com

Discovery of highly potent dual EP2and EP3agonists with subtype selectivity

The cyclic carbamate derivatives, 2-{[2-((4S)-4-{(1E,3R)-8-fluoro-3-hydroxy-4,4-dimethyl-1-octenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (5) and 2-{[2-((4S)-4-{(1E,3R)-3-[1-(4-fluorobutyl)cyclobutyl]-3-hydroxy-1-propenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (7) were identified as the first potent dual EP2and EP3agonists with selectivity against the EP1and EP4subtypes. Compounds 5 and 7 demonstrated highly potent dual EP2and EP3agonist activity with EC50values of 10 nM or less. In addition, these compounds possess structural features distinct from natural prostaglandins, such as a cyclic carbamate moiety, a dimethyl or cyclobutyl group and a terminal fluorine atom.

Synthesis and evaluation of a potent, well-balanced EP2/EP3 dual agonist

A highly potent and well-balanced dual agonist for the EP2 and EP3 receptors is described. Optimization of the lead compound was accomplished in consideration of the relative agonist activity against each EP subtype receptor and the pharmacokinetic profile. As the result, 2-[(2-{(1R,2R)-2-[(1E,4S)-5-cyclopentyl-4-hydroxy-4-methyl-1-penten-1-yl]-5-oxocyclopentyl}eth-yl)thio]-1,3-thiazole-4-carboxylic acid (10) showed excellent potency (human EC50 EP2 = 1.1 nM, EP3 = 1.0 nM) with acceptable selectivity over the EP1 and EP4 subtypes (>2000-fold). Further fine-tuning of compound 10 led to identification of ONO-8055 as a clinical candidate. ONO-8055 was effective at an extremely low dose (0.01 mg/kg, po, bid) in rats, and dose-dependently improved voiding dysfunction in a monkey model of underactive bladder (UAB). ONO-8055 is expected to be a novel and highly promising drug for UAB.

NOVEL BENZODIOXANE-PIPERIDINE DERIVATIVES AND THEIR THERAPEUTIC APPLICATIONS FOR TREATING NEUROPSYCHIATRIC DISORDERS

The present invention concerns benzodioxane-piperidine with general formula I: wherein notably: R1 represents one or more identical or different substituent(s) on the benzene ring, each independently representing a hydrogen or halogen atom, or a C1-4 alkyl group, or a C1-4 alkoxy group or a C1-4 hydroxyalkyl group or a C1-4 alkylcarbonyl or an alkoxycarbonyl group or an OH group or an SO2R group with R alkyl, or a CN group, or a CF3 group, or an OCF 3 group; n=1, 2 or 3;m=0 or 1, andR2 represents one or more identical or different substituent(s) on the oxazolidinone or morpholinone ring, each independently representing: a hydrogen atom, a C1-4 alkyl group, or a C1-4 alkoxy group, or a C1-4 hydroxyalkyl group, or an alkylcarbonyl group, or an alkoxycarbonyl group, or an alkoxyphenyl group.