56439-36-2

Upstream product

• 123-75-1 pyrrolidine 
• 1142-20-7 N-Cbz-Ala 
• 25172-67-2 Z-Ala-O-COO-isoBu 
• 65638-93-9 N-Carbobenzoxy-L-alanin-kohlensaeureaethylesteranhydrid 

Downstream Products

• 115200-95-8 2-(3,4-Dichloro-phenyl)-N-methyl-N-((S)-1-methyl-2-pyrrolidin-1-yl-ethyl)-acetamide 

Relevant academic research and scientific papers

Double axial chirality promoted asymmetric [2,3] Stevens rearrangement of N-cinnamyl l-alanine amide-derived ammonium ylides

The base-induced asymmetric [2,3] Stevens rearrangement of N-cinnamyl tetraalkylammonium ylides derived from l-alanine amides proceeds via a double axially chiral intermediate to afford the corresponding α-substituted alanine derivatives with high enantio- and diastereoselectivities. the Partner Organisations 2014.

Carboxamidation of carboxylic acids with 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) without bases

Formation of carboxamides of a variety of carboxylic acids with the coupling reagent BBDI is described. This procedure permits a one pot and simple operation without the need of any bases and no base was?required for even use of amine hydrochlorides. In addition, an approach to BBDI-catalyzed carboxamidation is examined.

Small peptides as modular catalysts for the direct asymmetric aldol reaction: Ancient peptides with aldolase enzyme activity

Simple peptides and their analogues having a primary amino group as the catalytic residue mediate the direct asymmetric intermolecular aldol reaction with high stereoselectivity and furnish the corresponding aldol products with up to 99% ee; this intrinsic ability of highly modular peptides may explain the initial molecular evolution of aldolase enzymes. The Royal Society of Chemistry 2005.

2-(3,4-Dichlorophenyl)-N-methyl-N-acetamides: The Use of Conformational Analysis in the Development of a Novel Series of Potent Opioid κ Agonists

This paper describes the synthesis of a series of N-acetamides (1), methylated at C1 and/or C2 of the ethyl linking group, and their biological evaluation as opioid κ agonists.Conformational analysis of corresponding desaryl analogues 2 suggested that only those compounds capable of occupying an energy minimum close to that of the known κ agonist N-acetamide U-50488 might possess κ agonist properties.Starting from chiral amino acids, other alkyl and aryl substituents were introduced at C1 of the ethyl-linking moiety, giving compounds capable of adopting the same conformation as U-50488.The most potent of these, 2-(3,4-dichlorophenyl)-N-methyl-N-acetamide (8), was 146-fold more active than U-50488 in vitro in the mouse vas deferens model and exhibited potent naloxone-reversible analgesic effects (ED50 = 0.004 mg/kg sc) in an abdominal constriction model.

Structure/Activity Studies Related to 2-(3,4-Dichlorophenyl)-N-methyl-N-acetamides: A Novel Series of Potent and Selective κ-Opioid Agonists

This paper describes the synthesis of a series of N-acetamides 1, variously substituted at the carbon adjacent to the amide nitrogen (C1), and related analogues, together with their biological evaluation as opioid κ agonists.In the first part of the study, the variants in N-acyl, N-alkyl, and amino functions were explored when the substituent at C1 was 1-methylethyl and the optimum was found to be exemplified by 2-(3,4-dichlorophenyl)-N-methyl-N-acetamide (13).Subsequently, racemic or chiral amino acids were used to introduce other alkyl and aryl substituents at C1 of the ethyl linking moiety.A series of potent compounds, bearing substituted-aryl groups at C1, were discovered, typified by 2-(3,4-dichlorophenyl)-N-methyl-N-acetamide (48), which was 5-fold more active as the racemate than 13 in vitro and exhibited potent naloxone-reversible analgesic effects (ED50 = 0.04 mg/kg sc) in a mouse abdominal constriction model.

Diamine compounds

Compounds of the general formula I wherein R1 represents an optionally substituted C6-10 aryl group, or R1 represents an optionally substituted 5- or 6--membered heterocyclic moiety;, X represents a single bond, -CH2-, -OCH2/su