65563-98-6

Upstream product

• 67-56-1 methanol 
• 7563-05-5 4,4-dimethyl-2-phenyl-5-oxazolone 
• 7244-67-9 N-benzoyl-L-alanine methyl ester 
• 57224-51-8 N-benzoyl-2-methylalanine 
• 15028-41-8 methyl 2-aminoisobutyrate hydrochloride 
• 98-88-4 benzoyl chloride 
• 13257-67-5 2-amino-2-methylpropionic acid methyl ester 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 2589-57-3 dimethyl 2,2'-azobis(isobutyrate) 
• 65-85-0 benzoic acid 
• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 74-88-4 methyl iodide 
• 1205-08-9 methyl hippurate 
• 7260-27-7 (R)-N-benzoylalanine methyl ester 

Downstream Products

• 1534329-08-2 methyl 2-methyl-2-(N-[¹¹C]methylbenzamido)propanoate 
• 861597-64-0 methyl 2-methyl-2-(N-methylbenzamido)propanoate 

Relevant academic research and scientific papers

Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole (TCB-OBt): observation of uncommon intermolecular oxygen-oxygen interaction and synthetic application in amidation

Herein, we investigated the supramolecular assembly of a modified Yamaguchi reagent TCB-OBt. Interestingly, each molecule is interconnected through novel chalcogen-chalcogen (O?O) interaction, π-π stacking, and aromatic C-H?O interaction. Hirshfeld surface analysis confirmed the existence of uncommon O?O interactions. A well-organized supramolecular layer structure and helical arrangement were observed in the crystal structure. TCB-OBt crystallized in the O-substituted desmotropic form. DFT calculations suggest that the O-substituted form is more stable than theN-substituted form (TCB-(N)-OBt). Morphology analysis indicates the formation of a fantastically well organized, continuous block-shaped system. Furthermore, the designed reagent works as an efficient activating reagent for amide bond formation with good yields under mild reaction conditions. Use of this reagent avoided intractable acid chlorides, and this new mixed-anhydride-based reagent may further be applicable for many other organic transformations.

Synthesis of N-alkyl-Cα,α-dimethylglycine derivatives

The application of trialkyloxonium tetrafluoroborates for N-alkylation of the nonnatural amino acid Cα, α-dimethylglycine is described. Several methyl esters of dimethylglycine protected with different amine protecting groups were subject to N-

The use of tetrabutylammonium fluoride to promote N- and O- 11C-methylation reactions with iodo[11C]methane in dimethyl sulfoxide

The N- or O-methylation reactions of compounds bearing amide, aniline, or phenol moieties using iodo[11C]methane (1) with the aid of a base are frequently applied to the preparation of 11C-labeled radiopharmaceuticals. Although sodiu

PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%.

Reaction of N-Benzoyl Amino Acids with Oxalyl Chloride: a Facile Route to 4-Substituted 2-Phenyloxazole-5-carboxylates

N-benzoyl amino acids 1a-g react with excess oxalyl chloride at room temperature followed by addition of alcohols to afford 4-substituted 2-phenyloxazole-5-carboxylates 3a-g.

SYNTHESIS OF α-SUBSTITUTED α-AMINO ACIDS BY THE ALKYLATION OF 5-OXAZOLINONE DERIVATIVES

Methods have been developed for the alkylation of 5-oxazolinone derivatives in DMF in the presence of K2CO3, KOH, or diisopropylethylamine and a phase transfer catalyst as well as for the preparation of α-methylphenylalanine, α-methylalanine, α-methylalanine, and the methyl ester of N-benzoyl-α-methylalanine.Increasing the initial concentration of the starting 5-oxazolinone in the reaction mixture leads to a sharp drop in the yield of reaction products due to side condensation reactions.The reaction of 2-phenyl-4-benzyl-5-oxazolinonewith ethyl iodide gave a dimer, mamely, 3-(benzoylamino)-3,5-dibenzylpyrrolidine-2,4-dione.

Selective Reaction of Glycine Residues in Hydrogen Atom Transfer from Amino Acid Derivatives

Relative rates of reaction of the N-benzoylamino acid methyl esters 1a-4a with N-bromosuccinimide and of 1a-4a with di-tert-butyl peroxide are reported.The selective reaction of glycine derivatives in these and other reactions of N-acylamino acid derivatives is attributed to the relative stability of intermediate radicals produced by hydrogen atom transfer.Radicals formed by hydrogen abstraction from N-acylglycine derivatives may adopt planar conformations which are relatively free of nonbonding interactions and in which there is maximum delocalization of the unpairedelectron, whereas radicals produced by similar reactions of derivatives of other amino acids are relatively unstable because of nonbonding interactions.In accord with this hypothesis, methyl pyroglutamate (5a) reacts at a faster rate than N-benzoylglycine methyl ester (1a) in reactions with either N-bromosuccinimide or di-tert-butyl peroxide.Anomalous rates of reaction of N-benzoylproline methyl ester (6a) are rationalized in terms of the regioselectivity of hydrogen atom transfer.Evidence for the mechanisms of reactions of 1a-6a is derived from product studies and by comparison of the relative rates of reactions of 1a-6a with those of the deuteriated amino acid derivatives 1b, 2b, 3b,c, 5b, and 6b,c.

Synthese von 3,3-Dimethylperhydro-1,4-diazepin-2,5,7-trionen aus 3-Dimethylamino-2,2-dimethyl-2H-azirin und Malonsaeuremonoamiden

Synthesis of 3,3-Dimethylperhydro-1,4-diazepin-2,5,7-triones from 3-Dimethylamino-2,2-dimethyl-2H-azirine and Malonic Acid Monoamides.Reaction of aminoazirine 1 and malonic acid monoamides 5 in CH3CN yielded triamides of type 6 (Scheme 2), which were transformed to the corresponding phenylthioates 9 by treatment of a solution of 6 and thiophenol in CH3CN with HCl (Scheme 4).Cyclization of 9 to give the 1,4-diazepin-2,5,7-trione of type 10 was achieved with NaH in toluene at about 90 deg.It has been shown that 2-oxazolin-5-ones are intermediates in the selective cleavage of the therminal amide function of 6 (Scheme 3).

AMIDOACETONE ENOLATE ANIONS: ALKYLATION AND MICHAEL REACTION

The lithyum enolate derived from benzamidoacetone (1) can be regiospecifically alkylated at C(1) and stereospecifically added in conjugate fashion to cyclohexenone without resorting to protection of free NH.Comparison is made with alkylations of methyl hippurate.