64282-11-7

Upstream product

• 64298-85-7 methyl-2-benzylideneamino-2-methyl-3-phenylpropanoate 
• 100-39-0 benzyl bromide 
• 120328-90-7 methyl (E)-N-benzylidenealaninate 
• 123761-22-8 methyl 2-(4-chlorobenzylidene)amino-2-methyl-3-phenylpropionate 
• 68870-85-9 methyl 2-(benzylideneamino)-3-phenylpropionate 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 

Downstream Products

• 88105-61-7 N-benzoyl-L-prolyl-DL-α-methylphenylalanine methyl ester 
• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 
• 38574-55-9 (R)-(-)-methyl 2-amino-2-methyl-3-phenylpropionate 
• 101210-80-4 2-methyl-3-phenyl-2-phthalimidopropanyl chloride 
• 101210-79-1 2-(2-carboxybenzamido)-2-methyl-3-phenylpropanoic acid 
• 101210-82-6 1-chloro-3-methyl-4-phenyl-3-phthalimidobutan-2-one 
• 101210-83-7 1-hydroxy-3-methyl-4-phenyl-3-phthalimidobutan-2-one 
• 101210-84-8 3-amino-1-hydroxy-3-methyl-4-phenylbutan-2-one hydrochloride 
• 101211-00-1 2-amino-6-(2-benzyl-4-hydroxy-3-oxobutan-2-ylamino)-5-nitropyrimidin-4(3H)-one 
• 101210-81-5 1-diazo-3-methyl-4-phenyl-3-phthalimodobutan-2-one 
• 101210-99-5 2-amino-6-(2-benzyl-4-hydroxy-3-oxobutan-2-ylamino)-5-nitropyrimidin-4(3H)-one semicarbazone 
• 101231-99-6 3-amino-1-hydroxy-3-methyl-4-phenylbutan-2-one semicarbazone hydrochloride 
• 16024-41-2 2-acetylamino-2-methyl-3-phenyl-propionic acid methyl ester 
• 27979-44-8 methyl 3-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 

Relevant academic research and scientific papers

Nitroxyl Catalysts for Six-Membered Ring Bromolactonization and Intermolecular Bromoesterification of Alkenes with Carboxylic Acids

We developed a nitroxyl-catalyzed bromoesterification of alkenes with bromo reagents, which includes a six-membered ring bromolactonization of alkenyl carboxylic acids catalyzed by AZADO as the nitroxyl radical catalyst, and an intermolecular bromoesterification of alkenes with carboxylic acids using NMO as the N-oxide catalyst. We also accomplished a remote diastereoselective bromohydroxylation via an AZADO-catalyzed six-membered ring bromolactonization and a subsequent ring cleavage reaction with alkylamines to furnish ?-bromo-δ-hydroxy amides with high diastereoselectivity.

Amine-Directed Palladium-Catalyzed C?H Halogenation of Phenylalanine Derivatives

An efficient primary-amine-directed, palladium-catalyzed C?H halogenation (X=I, Br, Cl) of phenylalanine derivatives is reported on a range of quaternary amino acid (AA) derivatives thanks to suitable conditions employing trifluoroacetic acid as additive. The extension of this original native functionality-directed ortho-selective halogenation was even demonstrated with the more challenging native phenylalanine as tertiary AA.

Preparation of Substituted Tetrahydroisoquinolines by Pd(II)-Catalyzed NH2-Directed Insertion of Michael Acceptors into C-H Bonds Followed by NH2-Conjugated Addition

3,3-Disubstituted tetrahydroisoquinolines are prepared in one step from Michael acceptors and 2-phenylethylamines under Pd catalysis and Ag2CO3 as an oxidant. Presumably, activation of an ortho C-H bond of the aromatic ring with Pd(II) is directed by the primary amine to form a palladacycle. Insertion of the olefin, subsequent conjugated addition of the amine, and reductive elimination of Pd(0) affords the expected products. Silver carbonate is not necessary when 2-phenylethylamines are converted previously to N-benzoyloxy-2-phenylethylamines.

NH2 as a directing group: From the cyclopalladation of amino esters to the preparation of benzolactams by palladium(II)-catalyzed carbonylation of N-unprotected arylethylamines

An unusual NH2-directed Pd(II)-catalyzed carbonylation of quaternary aromatic α-amino esters to yield benzolactams has been developed. The steric hindrance around the amino group is pivotal for the success of the process. The stoichiometric cyclometalation of a variety amino esters has been studied in order to evaluate the influence of the different variables (size of the metallacycle, aromatic ring substituents, and steric bulk) in the process, and a complete kinetico-mechanistic study of the cyclopalladation process has been carried out. The experimental results indicate that the full substitution of the carbon in the α position of the amino esters plays an important role in their cyclopalladation reaction. The reaction shows a strong bias toward six-membered lactams over the five-membered analogues, which can be explained by a greater reactivity of the six-membered palladacycles.

Influence of aromatic substituents on metal(II)salen catalysed, asymmetric synthesis of α-methyl α-amino acids

The influence of substituents on both the aromatic rings of the catalyst, and the benzylidene unit of the substrate are investigated in the (salen)copper(II) catalysed asymmetric benzylation of alanine derivatives. Catalysts with electron-donating, and el

Piperazine- and piperidine-derivatives as melanocortin receptor agonists

The present invention relates to melanocortin receptor agonists of formula I, which is useful in the treatment of obesity, diabetes and male and/or female sexual dysfunction.

Highly enantioselective alkylation of glycine methyl and ethyl ester derivatives under phase-transfer conditions: Its synthetic advantage

Phase-transfer alkylation of the benzophenone Schiff base of glycine methyl or ethyl ester (2) was found to be catalyzed by 3,4,5-F 3-C6H2-NAS-Br [(S,S)-1] with high efficiency and excellent enantioselectivity. This procedure allows facile derivatization of the resulting alkylation products to other synthetically useful chiral building blocks.

BENZAMIDINE DERIVATIVES SUBSTITUTED BY AMINO ACID AND HYDROXY ACID DERIVATIVES AND THEIR USE AS ANTI-COAGULANTS

This invention is directed to benzamidine derivatives substituted by amino acid and hydroxy acid derivatives which are useful as anti-coagulants. This invention is also directed to pharmaceutical compositions containing the compounds of the invention, and methods of using the compounds to treat disease-states characterized by thrombotic activity.

Preparation and use in amino acid synthesis of a new chiral glycine derivative - (R)- and (S)-tert-Butyl 2-tert-Butyl-4-methoxy-2,5-dihydroimidazole-1-carboxylate (BDI)

The title compound BDI is prepared on multigram scale, either by resolution of the precursor 2-tert-butylimidazolidin-4-one (from glycine amide and pivalaldehyde) through diastereomeric salts (Scheme 2) or by preparative chromatographic enantiomer separation on a chiral column. Lithiated BDI derivatives are highly nucleophilic species, combining the structural elements of a Li enaminate, of an enolether and of an N-Boc-enaminate (E, G). They react with complete diastereoselectivity (NMR analysis) from the face trans to the tert-butyl group. The electrophiles employed are primary and secondary alkyl, allyl, benzyl, and propargyl halides (Schemes 3 and 5), enoates (in Michael additions, Scheme 7), as well as aliphatic and aromatic aldehydes (in aldol additions, Scheme 8). When a third, exocyclic, stereocenter is formed in these reactions, there is a high degree of enantiomer differentiation (with tac. sec. halides, products 10-12) and of enantiotopic face differentiation (with enoates and aldehydes, products 40-50). The reactions are so clean that highly efficient in-situ double alkylations are feasible, in which the sequence of addition of the two different electrophiles determines the configuration at the newly formed stereogenic center (Scheme 5). In contrast to derivatives of previously reported chiral glycine reagents, the products from BDI are converted to methyl esters of amino acids under mild conditions and without concomitant formation (... and the need for recovery or removal) of a chiral auxiliary; the method is compatible with acid-sensitive side chains in the α-amino acids and α-branched α-amino acids to be synthesized (Schemes 4 and 6). The addition of Li-BDI to aldehydes furnishes, after hydrolysis, α-amino-β-hydroxy acids of erythro configuration (allo-threonine analogs, Scheme 8); a model for the stereochemical course of this reaction (rel. topicity unlike) is proposed, and compared with the corresponding conversions of analogous oxazolidinone and imidazolidinone Li enolates which occur with rel. topicity like.