70454-09-0

Basic information

• Product Name: ethyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate
• Synonyms: ethyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate
• CAS NO: 70454-09-0
• Molecular Formula: C₁₂H₁₃NO₂S
• Molecular Weight: 235.30212
• Mol File: 70454-09-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate(70454-09-0)
• EPA Substance Registry System: ethyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate(70454-09-0)

Safety Data

• Hazardous Substances Data: 70454-09-0(Hazardous Substances Data)

Upstream product

• 868-59-7 L-cysteine ethyl ester hydrochloride 
• 5873-90-5 methyl benzimidate hydrochloride 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 3411-58-3 L-cysteine ethylester 

Downstream Products

• 158785-69-4 rac-ethyl 4-methyl-2-phenylthiazoline-4-carboxylate 
• 59937-01-8 2-phenylthiazole-4-carboxylic acid ethyl ester 
• 70454-08-9 7-oxo-6-phenoxy-5-phenyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid ethyl ester 
• 62096-93-9 2-phenyl-4,5-dihydrothiazole-4-carboxylic acid 

Relevant articles and documents

Stereodivergent Desymmetrization of Simple Dicarboxylates via Branch-Selective Pd/Cu Catalyzed Allylic Substitution

Asymmetric desymmetrization has been demonstrated to be a powerful strategy for building stereocenters in asymmetric synthesis. Herein, a Pd/Cu catalyzed asymmetric desymmetrization reaction with a simple geminal dicarboxylate is reported. A wide scope of imino esters bearing an aryl or heteroaromatic group were compatible with this bimetallic catalytic system. The reactions proceeded smoothly, giving the desired products in good yields with high to excellent regio-, diastereo-, and enantioselectivity (up to 20 : 1 branched:linear, >20 : 1 dr, >99 % ee). Notably, the reaction favored branched selectivity, which is unusual for the Pd-catalyzed allylic alkylation reaction. In addition, the standard product could be easily transformed to other valuable molecules such as chiral allylic alcohols, carbamates, and organic boron compounds. Furthermore, DFT calculations were conducted to explain the origin of the branched selectivity.

PROCESS FOR PRODUCING OPTICALLY ACTIVE ALPHA-SUBSTITUTED CYSTEINE OR SALT THEREOF, INTERMEDIATE THEREFOR, AND PROCESS FOR PRODUCING THE SAME

The present invention provides a simple, practical, and industrially advantageous process for producing an optically active α-substituted cysteine or a salt thereof from inexpensive and readily available materials.The present invention provides a process for producing an optically active α-substituted cysteine or a salt thereof by converting a cysteine derivative into a thiazoline compound and subjecting the resulting thiazoline compound to a stereoselective substituent-introducing reaction catalyzed by an optically active quaternary ammonium salt, in particular, an axially asymmetric quaternary ammonium salt to produce an optically active thiazoline compound and then hydrolyzing the resulting thiazoline compound.

Synthesis and Nuclear Magnetic Resonance Study of 2-Thiazolines

A series of 5,5-dimethyl-2-thiazoline-4-carboxylates with a phenyl or methyl group at the 2-position of the ring were prepared from the corresponding methyl or ethyl ester of penicillamine and either methyl benzimidate or ethyl acetimidate.The free acid was obtained by the reaction of penicillamine with benzonitrile to produce 5,5-dimethyl-2-phenyl-2-thiazoline-4-carboxylic acid.Corresponding thiazolines were prepared from cysteine in the same manner.The nuclear magnetic resonance spectra of both series exhibit coupling of the methyl group at the 2-position with the hydrogen at the 4-position.The groups at the 5-position are nonequivalent and in the case of the cysteine series give rise to an ABX system.Further analysis confirms a concentration dependence for this splitting pattern.