22887-53-2

Upstream product

• 13450-77-6 4-chlorohippuric acid 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 21336-78-7 2-(4-chloro-phenyl)-4-[2-(1-methyl-1H-naphtho[1,2-d]oxazol-2-ylidene)-ethylidene]-4H-oxazol-5-one 
• 32603-58-0 2-(4-chloro-phenyl)-4-[2-(3-methyl-3H-naphtho[2,1-d]oxazol-2-ylidene)-ethylidene]-4H-oxazol-5-one 
• 22851-58-7 2-(p-Chlorbenzamido)-3-dimethylamino-propionsaeure 
• 80353-50-0 N-<2-(3,4-Dimethylphenyl)-2-oxoethyl>-4-chlorobenzamide 
• 80353-51-1 N-<2-(2,5-Dimethylphenyl)-2-oxoethyl>-4-chlorobenzamide 
• 13450-77-6 4-chlorohippuric acid 
• 59490-25-4 α-(4-chloro-benzoylamino)-trans-cinnamic acid 
• 1360824-99-2 (1R,3aS,6aR)-4,6-dioxo-3-(4-chlorophenyl)-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylic acid methyl ester 
• 99973-54-3 4-ethylidene-2-(4-chloro-phenyl)-4H-oxazol-5-one 
• 34108-14-0 4-((Z)-benzylidene)-2-(4-chloro-phenyl)-4H-oxazol-5-one 

Relevant academic research and scientific papers

Catalytic Asymmetric Synthesis of anti-α,β-Diamino Acid Derivatives

A novel approach to chiral anti-α,β-diamino acid derivatives through tandem orthogonal organocatalysis has been developed. Chiral phosphoric acid catalysts control the chemo-, regio-, and stereoselective addition of hydroxylamines to alkylideneoxazolones, while a phosphine catalyst promotes the isomerization of Z- alkylideneoxazolones to the more reactive E- alkylideneoxazolones. (Chemical Equation Presented).

E-Z ratio and stability of halogenated benzylidene derivatives formed during the detection of glycine conjugates

The orange fluorescing spot formed during the detection of halogenated hippuric acids with 4-N,N-Dimethylaminobenzaldehyde on TLC-plates consists of a E/Z-mixture of the corresponding benzyliden derivatives. Intermediates are the azlactones.

A kinetic study of the base-catalyzed dimerization of 5(4H)-oxazolones

The effects of the substituent at position-2 and kind of the base on the rate of the base-catalyzed dimerization of 5(4H)-oxazolones have been investigated. The electrondonating and strong steric effect of the substituent at position-2 reduce markedly the proclivity of 5(4H)-oxazolones to dimerization. The following catalytic activity sequence of the bases has been found: DBU >> Et3N > (i-Pr)2EtN.

Structure-Reactivity Studies on the Equilibrium Reaction between Phenolate Ions and 2-Aryloxazolin-5-ones: Data Consistent with a Concerted Acyl-Group-Transfer Mechanism

The rate and equilibrium constants for the reaction between phenolate anions and 2-aryloxazolin-5-ones have been measured as a function of the structures Ar and Ar'.The change in "effective" charge on both phenol-leaving oxygen and endocyclic oxygen from ground to transition state, as determined from the relevant Broensted parameters, is substantial and essentially additive consistent with a concerted displacement mechanism.The stepwise mechanism requires a small change in effective charge on the phenol oxygen because departure of phenolate ion from the tetrahedral intermediate cannot be rate limiting.Hydroxide ion attack on the C-5 atom of the oxazolinone to yield a benzoylglycine has a Hammett ?- dependence which can only arise from a concerted displacement; the rate-limiting step for the stepwise mechanism is the addition of hydroxide and the transition state of the rate-limiting step will therefore not involve much endocyclic C-O bond fission.An inverse deuterium oxide solvent isotope effect indicates that the observed general-acid catalysis has a specific-acid/nucleophilic mechanism; both hydroxide and oxonium ion catalysis are demonstrated by using 18O-labeling experiments to involve nucleophilic attack at the carbonyl (C-5) center.The equilibrium constant for reaction of azide ion with 2-phenyloxazolin-5-ones has been measured; it is suggested that the absence of racemization during azide coupling in peptide synthesis is related to the very unfavorable equilibrium constant for oxazolinone formation compared with that of activated oxygen esters.