75152-18-0

Upstream product

• 27115-50-0 N-(4-methylbenzoyl)glycine 
• 75152-14-6 (4-Methyl-benzoylamino)-acetic acid 4-nitro-phenyl ester 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 72615-38-4 (4Z)-2-(4-methylphenyl)-4-(phenylmethylidene)-1,3-oxazol-5(4H)-one 
• 107871-15-8 4-ethylidene-2-p-tolyl-4H-oxazol-5-one 
• 21336-76-5 4-[2-(1-methyl-1H-naphtho[1,2-d]oxazol-2-ylidene)-ethylidene]-2-p-tolyl-4H-oxazol-5-one 
• 21335-22-8 4-[2-(3-methyl-3H-naphtho[2,1-d]oxazol-2-ylidene)-ethylidene]-2-p-tolyl-4H-oxazol-5-one 
• 27115-50-0 N-(4-methylbenzoyl)glycine 
• 1360824-98-1 (1R,3aS,6aR)-4,6-dioxo-3-(4-methylphenyl)-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylic acid methyl ester 
• 1355332-97-6 ethyl 2-(2-(p-tolyl)oxazol-5-yl)acetate 
• 1206981-95-4 2-(2-(p-tolyl)oxazol-5-yl)acetonitrile 
• 96907-63-0 2,5-bis-(4-methylphenyl)oxazole 
• 16155-60-5 5-phenyl-2-p-tolyloxazole 
• 82221-14-5 4-Methyl-N-[1-(2-oxo-2-phenylethyl)]benzamide 
• 96907-78-7 4-methyl-N-(2-oxo-2-(4-methylphenyl)ethyl)benzamide 

Relevant academic research and scientific papers

One-pot synthesis of 2,4,5-trisubstituted oxazoles from N-acyl amino acids by a combination of cyclodehydration with N,N′-diisopropylcarbodiimide and Wittig olefination

By a combination of cyclodehydration of N-acyl amino acids with N,N′-diisopropylcarbodiimide (DIC) and non-classical Wittig olefination of the resultant 5(4H)-oxazolones with Ph3PCHCN and Ph 3PCHCOOEt, 5-oxazoleacetonitriles and 5-oxazoleacetates were synthesized in one-pot in 41-85% and 57-70% yields, respectively.

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.