40216-62-4

Upstream product

• 4070-48-8 L-Valine methyl ester 
• 100-52-7 benzaldehyde 
• 13803-83-3 methyl (S)-2-(benzylideneamino)-3-methylbutanoate 
• 106-95-6 allyl bromide 
• 100-39-0 benzyl bromide 
• 72-18-4 L-valine 
• 6306-52-1 L-valine methylester hydrochloride 
• 198836-33-8 methyl (S)-3-methyl-2-(2-nitrophenylsulfonamido)butanoate 
• 75-77-4 chloro-trimethyl-silane 
• 130608-02-5 methyl N-benzylidene-L-valinate 
• 198836-40-7 N-benzyl-N-(2-nitrophenylsulfonyl)-L-valine methyl ester 
• 13803-83-3 methyl 2-(benzylideneamino)-3-methylbutanoate 
• 3952-67-8 methyl 3-methyl-2-ketobutanoate 
• 100-46-9 benzylamine 

Downstream Products

• 912998-94-8 2-[benzyl(4-fluorobenzoyl)amino]-3-methylbutanoic acid 
• 1052703-92-0 C₁₈H₂₅NO₅ 
• 900187-89-5 (S)-methyl N-benzyl-N-(tert-butoxycarbonyl)valinate 
• 118460-23-4 (S)-methyl 2-(benzyl(methyl)amino)-3-methylbutanoate 
• 5619-05-6 DL-valine methyl ester hydrochloride 
• 1403983-89-0 2-[benzyl(methyl)amino]-3-methyl-1,1-diphenylbutan-1-ol 
• 129156-92-9 N-benzyl-N-[(1S)-1-(methoxymethyl)-2-methylpropyl]amine 
• 433735-11-6 1-[(3'R,6'S)-1'-benzyl-3'-benzyloxycarbonylmethyl-5'-ethoxy-(6'H)-6'-isopropylpyrazin-3'-yl-2'-one]-3-[(3''R,6''S)-1''-benzyl-5''-ethoxy-3'',6''-dihydro-6''-isopropylpyrazin-3''-yl-2''-one]propane 

Relevant academic research and scientific papers

Electroreductive intramolecular coupling of chiral α-imino esters: Stereoselective synthesis of mixed ketals of cis-2,4-disubstituted azetidine-3-ones

The electroreduction of chiral aromatic α-imino esters prepared from (S)-α-amino acids, such as (S)-valine, (S)-leucine, and (S)-phenylalanine, in the presence of chlorotrimethylsilane and triethylamine afforded four-membered cyclized products, mixed ketals of cis-2,4-disubstituted azetidine-3-ones, stereospecifically (>99% de, 85-99% ee). The best result of the electroreductive cyclization was obtained using Bu4NClO 4 as a supporting electrolyte and a Pt cathode. The absolute stereochemistry of the obtained single stereoisomers was confirmed to be 2R,3R,4S by X-ray crystallography. Calculations for the transition states of the cyclization support the stereospecific formation of the (2R,3R,4S)-isomers.

ANTIVIRAL COMPOUNDS

The present invention relates to novel compounds of general formula (I) wherein the groups X, and R1 to R4 have the meanings given in the description and claims, process for preparing these compounds and their use as for treating, preventing or ameliorating viral infections and their use for treating, preventing or ameliorating diseases which are associated with PLA2G16.

Main-Group-Catalyzed Reductive Alkylation of Multiply Substituted Amines with Aldehydes Using H2

Given the growing demand for green and sustainable chemical processes, the catalytic reductive alkylation of amines with main-group catalysts of low toxicity and molecular hydrogen as the reductant would be an ideal method to functionalize amines. However, such a process remains challenging. Herein, a novel reductive alkylation system using H2 is presented, which proceeds via a tandem reaction that involves the B(2,6-Cl2C6H3)(p-HC6F4)2-catalyzed formation of an imine and the subsequent hydrogenation of this imine catalyzed by a frustrated Lewis pair (FLP). This reductive alkylation reaction generates H2O as the sole byproduct and directly functionalizes amines that bear a remarkably wide range of substituents including carboxyl, hydroxyl, additional amino, primary amide, and primary sulfonamide groups. The synthesis of isoindolinones and aminophthalic anhydrides has also been achieved by a one-pot process that consists of a combination of the present reductive alkylation with an intramolecular amidation and intramolecular dehydration reactions, respectively. The reaction showed a zeroth-order and a first-order dependence on the concentration of an imine intermediate and B(2,6-Cl2C6H3)(p-HC6F4)2, respectively. In addition, the reaction progress was significantly affected by the concentration of H2. These results suggest a possible mechanism in which the heterolysis of H2 is facilitated by the FLP comprising THF and B(2,6-Cl2C6H3)(p-HC6F4)2.

Chiral-pool synthesis of 1,2,4-trisubstituted 1,4-diazepanes as novel σ1 receptor ligands

Starting from enantiomerically pure amino acids, 1,4-diazepanes with various substituents in 1, 2, and 4-position were synthesized following the late stage diversification strategy. The key step in the formation of the seven-membered ring was the intramolecular EDC coupling of amino acids 15, 26, and 39. The configuration in 2-position does not influence the σ1 affinity and selectivity over related receptors. A cyclohexylmethyl or a butyl group are the preferred substituents in 4-position, whereas a methyl moiety in 2-position and a (substituted) benzyl moiety in 1-position result in the highest σ1 affinity. These results fit nicely to the reported σ1 pharmacophore models. The compounds did not inhibit the structurally related fungal enzyme sterol Δ8,7-isomerase, but showed inhibition of diverse enzymes in late cholesterol biosynthesis at high concentrations. In a screening against more than 50 target proteins, (2S)-1-benzyl-4-(4-methoxybenzyl)-2-methyl-1,4-diazepane ((S)-28b, Ki(σ1) = 0.86 nM) showed a clean receptor profile. The dose dependent potentiation of electrically stimulated contractions of guinea pig vas deferens indicates σ1 agonistic activity of (S)-28b. Even at a dose of 100 mg/kg (S)-28b did not induce severe toxic or behavioral effects in the Irwin screen. Clear cognition enhancing effects were observed for (S)-28b after inducing amnesia by scopolamine.

(η5-Pentamethylcyclopentadienyl)iridium Complex Catalyzed Imine Reductions Utilizing the Biomimetic 1,4-NAD(P)H Cofactor and N-Benzyl-1,4-dihydronicotinamide as the Hydride-Transfer Agent

The interaction between synthetic organometallic complexes and metabolic cofactors has proven to be a newly emerging topic in bioorganometallic chemistry. Thus, the first cationic Cp*Ir-catalyzed (Cp=η5-pentamethylcyclopentadienyl) imine reduction in neutral buffered aqueous medium was examined. The reaction was found to proceed through hydride transfer from NADH as the hydride source at room temperature in air. Cationic Cp*Ir complexes proved to be the most efficient catalysts for this transformation. We also highlighted that the choice of the proton source was essential. The method was subsequently applied to cyclic and noncyclic imines. Eventually, the concept was extended to the reductive alkylation of one amine.

THERAPEUTIC COMPOUNDS AS INHIBITORS OF THE OREXIN-1 RECEPTOR

The present invention relates to compounds that are inhibitors of the orexin-1 receptor. The compounds have the structural formula I defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of diseases or disorders associated with orexin-1 receptor activity.

Preparation of the optically pure N-methyl amino ester method and product

The invention belongs to the field of organic synthesis of amino acids and discloses a method for preparing optically pure N-methyl amino-acid ester. The method comprises the following steps of carrying out esterification reaction on amino acid as a starting raw material and aldehyde to form an imine intermediate, carrying out reductive amination in the presence of palladium carbon, and carrying out hydrogenation and debenzylation to finally synthesize optically pure N-methyl amino-acid ester. The method has the advantages of simplicity in method, mild reaction conditions and good adaptability and side chains of D-type or L-type amino acid do not need to be protected.

Selective oxidation of amines to aldehydes or imines using laccase-mediated bio-oxidation

An efficient and practical chemo-enzymatic aerobic oxidation in water of benzylamines to obtain aldehydes or imines is described. Laccase from Trametes versicolor was chosen as biocatalyst, and TEMPO (radical 2,2,6,6-tetramethylpiperidine 1-oxyl) as mediator. A study on the pH dependence of the aqueous medium allowed us to realise a fine tuning on product selectivity. Under our optimized reaction conditions, the bio-oxidation of a series of primary, secondary and cyclic amines has been achieved.

Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: An easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine

Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized within 5 min to 2 h in high yields from easily accessible (S)-amino acid derived chiral carbocations. The diastereoselective Friedel-Crafts reaction is promoted by a Lewis acid (AlCl3) offering trans-diastereoselectivity. The rate of the reaction and diastereoselectivity of the product are significantly influenced by steric hindrance of the amino acids substituents and aryl groups. The methodology can be applied for the synthesis of the enantiomerically enriched bioactive scaffold (3S,4R)-demethoxy-3-isopropyl diclofensine. This journal is

Diastereoselective intramolecular allyl transfer from allyl carbamate accompanied by 5-endo-trig ring closure

To All(oc) involved: A palladium-catalyzed formal 5-endo-trig heteroannulation of enones generated in situ from amino acid derived β-keto nitriles has been realized (see scheme; Alloc=allyl carbamate). The reaction proceeds with allyl-group transfer from the carbamate protecting group to generate two new contiguous stereocenters, including one quaternary center, with high selectivity. Copyright