60437-56-1

Upstream product

• 616-45-5 2-pyrrolidinon 
• 645-45-4 hydrocinnamic acid chloride 
• 100-51-6 benzyl alcohol 
• 501-52-0 3-Phenylpropionic acid 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 151647-54-0 3-phenyl-1-pyrrolidin-1-yl-propane-1-one 
• 501-52-0 3-Phenylpropionic acid 
• 10264-11-6 N‐butyl‐3‐phenylpropanamide 
• 2021-28-5 ethyl dihydrocinnamate 
• 43125-06-0 1-cyclohexyl-3-phenyl-1-propanone 

Relevant academic research and scientific papers

Direct N-acylation of lactams, oxazolidinones, and imidazolidinones with aldehydes by Shvo's catalyst

Direct N-acylation of lactams, oxazolidinones, and imidazolidinones was achieved with aldehydes by Shvo's catalyst without using any other stoichiometric reagent. The N-acylations with α,β-unsaturated aldehydes were achieved with excellent yields.

Amide and lactam hydrolysis of N-(2-hydroxyacetyl)-2-pyrrolidone: Effective catalysis

When N-(2-hydroxyacetyl)-2-pyrrolidone (open form) is dissolved in water at pH > 8, irreversible cleavage of the exocyclic and endocyclic amide C - N bond occurs. The latter rupture corresponds to the lactam opening yielding N-(4-hydroxyacetyl)butanoic acid (NBA). NBA is produced from the ester hydrolysis of the esteramide macrocycle that is in equilibrium with the cyclol form of the open form. We have previously reported this latter equilibrium for N-(2-aminoacetyl)-2-lactams. 2-pyrrolidone (lactam) and glycolic acid are produced from direct hydrolysis of the open form by means of the amide exocyclic cleavage. The [NBA]/[lactam] ratio increases at higher pH since the NBA production is second order with respect to [OH-] while the corresponding lactam formation is only first order. The obtained kobs is hence the sum of the rate constants that yield lactam and NBA, respectively. This kobs is uncatalyzed and specific base catalyzed with unusually high rate constants of 2.1 × 10-6s-1 and 0.025 M-1 s -1, respectively. The stability of the corresponding tetrahedral intermediate formed and the intramolecular alkoxy nucleophilic attack on the lactam carbonyl group combined with an effective protonation of the lactam nitrogen that promotes the C - N cleavage, contribute to increase the reaction rates and lactam opening. Rate constants for the two parallel reactions are obtained from kobs and [NBA]/[lactam] versus pH plots. Copyright