155884-24-5

Basic information

• Product Name: 4-Oxazolecarboxylicacid,2-(1-methylethyl)-,methylester(9CI)
• Synonyms: 4-Oxazolecarboxylicacid,2-(1-methylethyl)-,methylester(9CI);Methyl 2-isopropyloxazole-4-carboxylate
• CAS NO: 155884-24-5
• Molecular Formula: C₈H₁₁NO₃
• Molecular Weight: 169.18
• Product Categories: ISOPROPYL
• Mol File: 155884-24-5.mol

Chemical Properties

• Boiling Point: 214.3±13.0 °C(Predicted)
• Appearance: /
• Density: 1.102±0.06 g/cm3(Predicted)
• PKA: -0.79±0.10(Predicted)
• CAS DataBase Reference: 4-Oxazolecarboxylicacid,2-(1-methylethyl)-,methylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxazolecarboxylicacid,2-(1-methylethyl)-,methylester(9CI)(155884-24-5)
• EPA Substance Registry System: 4-Oxazolecarboxylicacid,2-(1-methylethyl)-,methylester(9CI)(155884-24-5)

Safety Data

• Hazardous Substances Data: 155884-24-5(Hazardous Substances Data)

Upstream product

• 155884-30-3 4-carbomethoxy-2-isopropyl-2-oxazoline 
• 162739-76-6 methyl (4S)-4,5-dihydro-2-(1-methylethyl)oxazole-4-carboxylate 
• 153180-28-0 Diethyl <(isobutyryl)amino>malonate 
• 153180-11-1 Dimethyl <(phenylthio)methyl>malonate 
• 162740-05-8 N-isobutyryl-L-serine methyl ester 

Downstream Products

• 153180-21-3 2-Isopropyl-4-oxazolecarboxylic acid 
• 162740-03-6 4-(hydroxymethyl)-2-isopropyloxazole 
• 153180-19-9 N-<1',1'-Bis(methoxycarbonyl)-2'-(phenylthio)ethyl>-2-isopropyloxazole-4-carboxamide 
• 153180-35-9 2'-Isopropyl-5-phenylsulfanyl-[2,4']bioxazolyl-4,4-dicarboxylic acid dimethyl ester 
• 153180-36-0 2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester 
• 153180-20-2 N-<1'',1''-Bis(methoxycarbonyl)-2''-(phenylthio)ethyl>-2'-isopropyl-<2,4'-bioxazole>-4-carboxamide 
• 1429557-23-2 (R)-(3-(2-isopropyloxazol-4-yl)-8-methyl-5,6-dihydro-[1,2,4]-triazolo[4,3-a]pyrazin-7(8H)-yl)(4-(thiophen-2-yl)phenyl)methanone 

Relevant articles and documents

Widely Exploited, Yet Unreported: Regiocontrolled Synthesis and the Suzuki–Miyaura Reactions of Bromooxazole Building Blocks

An approach to synthesis of 2-, 4-, and 5-bromooxazoles is described. The method was optimized, and its scope was extended to all three isomeric parents, as well as various alkyl- and aryl-substituted bromooxazoles. It was found that direct regiocontrolled lithiation followed by reaction with electrophilic bromine source was common for all substrates and led exclusively to the target substituted 2-, 4- and 5-bromooxazoles on multigram scale. The utility of the multipurpose building blocks obtained in this work was demonstrated in the Suzuki–Miyaura cross-coupling reaction under parallel synthesis conditions.

Discovery of ritonavir, a potent inhibitor of HIV protease with high oral bioavailability and clinical efficacy

The structure-activity studies leading to the potent and clinically efficacious HIV protease inhibitor ritonavir are described. Beginning with the moderately potent and orally bioavailable inhibitor A-80987, systematic investigation of peripheral (P3 and P2') heterocyclic groups designed to decrease the rate of hepatic metabolism provided analogues with improved pharmacokinetic properties after oral dosing in rats. Replacement of pyridyl groups with thiazoles provided increased chemical stability toward oxidation while maintaining sufficient aqueous solubility for oral absorption. Optimization of hydrophobic interactions with the HIV protease active site produced ritonavir, with excellent in vitro potency (EC50 = 0.02 μM) and high and sustained plasma concentrations after oral administration in four species. Details of the discovery and preclinical development of ritonavir are described.

Oxidation of oxazolines and thiazolines to oxazoles and thiazoles. Application of the Kharasch-Sosnovsky reaction

Using a modification of the Kharasch-Sosnovsky reaction, the oxidation of oxazolines and thiazolines bearing a variety of 2-alkyl substituents (chiral and achiral) were smoothly oxidized to their corresponding oxazoles and thiazoles, respectively. The key feature involved in the successful implementation of this important oxidation was the use of a mixture of Cu(I) and Cu(II) salts to enhance the oxidation of the intermediate captodative radical, 24. The main limitation of this method was shown when the oxidation failed with oxazolines/thiazolines lacking the carboalkoxy group at C-4.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A retroviral protease inhibiting compound of the formula: STR1 is disclosed wherein R 1, R 2, R 5, R 6, Y m and Y' n are herein defined.

The Oxidation of 2-Oxazolines to 1,3-Oxazoles

Oxazolines are readily oxidized to 1,3-oxazoles using NBS/peroxide or light or, more efficiently, by the Kharasch-Sosnovsky Reaction.

Dimethyl Aminomalonate: A Useful C-3 Unit in a Mild, Direct Synthesis of Oxazole-4-carboxylates

N-Acyl derivatives of the title compound undergo oxidative cyclization upon treatment with N-chlorosuccinimide in DMF to form dimethyl 4,5-dihydro-5-(phenylthio)oxazole-4,4-dicarboxylates 4 which then are decarbomethoxylated with concomitant loss of thiop