64562-95-4

Usage

Uses

Used in Pharmaceutical Industry:
Methyl N-[(benzyloxy)carbonyl]alaninate is used as a key intermediate in the synthesis of various drugs and biologically active molecules. Its ability to participate in a wide range of chemical reactions, such as peptide coupling and esterification, makes it an indispensable component in the development of new pharmaceuticals.
Used in Organic Synthesis:
In the field of organic synthesis, methyl N-[(benzyloxy)carbonyl]alaninate is utilized as a versatile building block for the creation of complex organic compounds. Its reactivity and the presence of the benzyloxy carbonyl group allow for selective reactions and functional group transformations, contributing to the synthesis of a diverse array of organic molecules.
Used in Protecting Group Chemistry:
Methyl N-[(benzyloxy)carbonyl]alaninate is employed as a protecting group for the amine functionality in organic synthesis. The benzyloxy carbonyl group serves to shield the amine group, enabling selective reactions to occur at other sites within the molecule. This selective protection is crucial for the successful synthesis of complex organic compounds and the development of advanced pharmaceuticals.

Upstream product

• 4132-86-9 N-benzyloxycarbonylalanine 
• 74-88-4 methyl iodide 
• 110-05-4 di-tert-butyl peroxide 
• 1212-53-9 methyl N-benzyloxycarbonylglycinate 
• 108-88-3 toluene 
• 121809-09-4 {(N-carbobenzoxyamino)methylcarbene}pentacarbonylchromium⁽⁰⁾ 
• 21149-17-7 methyl 2-(benzyloxycarbonylamino)acrylate 
• 100-51-6 benzyl alcohol 
• 7625-53-8 D-alanine methyl ester 
• 501-53-1 benzyl chloroformate 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 2449-05-0 dibenzyl azodicarboxylate 
• 186581-53-3 diazomethane 
• 79-22-1 methyl chloroformate 

Downstream Products

• 92034-19-0 N-benzyloxycarbonyl-alanine-(2-hydroxy-ethylamide) 
• 1448603-18-6 (R)-benzyl (1-oxo-1-(prop-2-yn-1-ylamino)propan-2-yl)carbamate 
• 1448603-38-0 (R)-benzyl 1-{[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amino}-1-oxopropan-2-ylcarbamate 
• 176894-58-9 (2R)-2-(benzyloxycarbonylamino)propionitrile 
• 34276-31-8 benzyl N-[(1R)-1-(1H-1,2,3,4-tetrazol-5-yl)ethyl]carbamate 
• 129474-02-8 Cbz-D-Ala-L-Pro-NH₂ 
• 151378-81-3 benzyl [(1R)-2-amino-1-methyl-2-oxoethyl]carbamate 

Relevant academic research and scientific papers

Electrochemical Dimethyl Sulfide-Mediated Esterification of Amino Acids

Dimethyl sulfide-mediated electrochemical synthetic strategy for esterification of amino acids has been reported. A series of amino acids could react smoothly with alcohols, affording the desired esterification products with good efficiency. Importantly, the tolerance of peptides and gram-scale synthesis shed light on the utility of this protocol. Mechanistically, the dimethyl sulfide as a mediator plays an essential role in the transformation of amino acids.

Substituted macrocyclic tyrosine kinase inhibitor and application thereof

The invention belongs to the technical field of medicines, and particularly relates to a substituted macrocyclic tyrosine kinase inhibitor compound, and pharmaceutically acceptable salts and stereoisomers thereof. More specifically, the tyrosine kinase is

Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines

α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.

C-terminal 1-aminoethyltetrazole-containing oligopeptides as novel alanine racemase inhibitors

In clinical culture media inoculated with patient samples, selective inhibition of commensal bacteria is essential for accurate diagnosis and effective treatment, as they can mask the presence of pathogenic bacteria. The alanine analogue, 1-aminoethyltetr

2,4-Diamino-8-quinazoline carboxamides as novel, potent inhibitors of the NAD hydrolyzing enzyme CD38: Exploration of the 2-position structure-activity relationships

Starting from 4-amino-8-quinoline carboxamide lead 1a and scaffold hopping to the chemically more tractable quinazoline, a systematic exploration of the 2-substituents of the quinazoline ring, utilizing structure activity relationships and conformational constraint, resulted in the identification of 39 novel CD38 inhibitors. Eight of these analogs were 10–100-fold more potent human CD38 inhibitors, including the single digit nanomolar inhibitor 1am. Several of these molecules also exhibited improved therapeutic indices relative to hERG activity. A representative analog 1r exhibited suitable pharmacokinetic parameters for in vivo animal studies, including moderate clearance and good oral bioavailability. These inhibitor compounds will aid in the exploration of the enzymatic functions of CD38, as well as furthering the study of the therapeutic implications of NAD enhancement in metabolic disease models.

Amidation of unactivated ester derivatives mediated by trifluoroethanol

A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity.

Catalytic, highly enantioselective, direct amination of enecarbamates

Amination of enecarbamates with dibenzylazodicarboxylate and oxygenated nucleophiles in the presence of a catalytic amount of chiral phosphoric acid afforded optically active stable precursors of α-hydrazinoimines, which were reduced or oxidized, respectively, to vicinal diamines or α-amino acid precursors with excellent yield and enantioselectivity. This journal is

Carica papaya lipase catalysed resolution of β-amino esters for the highly enantioselective synthesis of (S)-dapoxetine

An efficient synthesis of the (S)-3-amino-3-phenylpropanoic acid enantiomer has been achieved by Carica papaya lipase (CPL) catalysed enantioselective alcoholysis of the corresponding racemic N-protected 2,2,2-trifluoroethyl esters in an organic solvent. A high enantioselectivity (E > 200) was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. Based on the resolution of a series of amino acids, it was found that the structure of the substrate has a profound effect on the CPL-catalysed resolution. The enantioselectivity and reaction rate were significantly enhanced by switching the conventional methyl ester to an activated trifluoroethyl ester. When considering steric effects, the substituted phenyl and amino groups should not both be large for the CPL-catalysed resolution. The mechanism of the CPL-catalysed enantioselective alcoholoysis of the amino acids is discussed to delineate the substrate requirements for CPL-catalysed resolution. Finally, the reaction was scaled up, and the products were separated and obtained in good yields (≥ 80 %). The (S)-3-amino-3- phenylpropanoic acid obtained was used as a key chiral intermediate in the synthesis of (S)-dapoxetine with very high enantiomeric excess (> 99 %). A carica papaya lipase catalysed resolution of N-protected β-phenylalanine esters has been developed. High enantioselectivity was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. After 50 % conversion, the products were separated and used as key chiral intermediates for the synthesis of (S)-dapoxetine with > 99 % ee. Copyright

The method of preparation of enantiomerically enriched products of condensation from racemic acids or acids of the low enentiomeric purity

The method of obtaining enantiomerically enriched condensation products consists of subjecting a racemic acid or an acid of low enantiomeric purity to the action of a condensing reagent - a chiral N-triazinylammonium tetrafluoroborate (formula 1), a chira

Modular P-OP ligands in rhodium-mediated asymmetric hydrogenation: A comparative catalysis study

Highly efficient and enantioselective hydrogenation reactions for α-(acylamino)acrylates, itaconic acid derivatives and analogues, α-substituted enol ester derivatives, and α-arylenamides (25 substrates) catalyzed by chiral cationic rhodium complexes of a set of P-OP ligands have been developed. The catalytic systems derived from these P-OP ligands provided a straightforward access to enantiomerically enriched α-amino acid, carboxylic acid, amine, and alcohol derivatives that are valuable chiral building blocks. Excellent efficiencies (full conversion in all cases) and extremely high enantiomeric excesses (94-99% ee) were achieved for a wide range of α-substituted enol ester derivatives, regardless of the substitution pattern. The R-oxy group of the ligand (methoxy or triphenylmethoxy) strongly influences the enantioselectivity and catalytic activity. Greater steric bulk around the metal centre correlated to greater (or similar) enantioselectivity, but also to slower hydrogenation. Furthermore, the hydrogenation rates observed with the four model substrates follow the same trend, independently of the R-oxy group of the ligand: methyl 2-acetamidoacrylate>dimethyl itaconate>1-phenylvinyl acetate>N-(1- phenylvinyl)acetamide. A substrate-to-catalyst ratio (S/C) of up to 10,000:1 was sufficient for total hydrogenation of a model substrate of intermediate reactivity (dimethyl itaconate), and did not imply any loss in conversion or enantioselectivity. Copyright