219835-31-1

Usage

Uses

Used in Organic Synthesis:
N-[(1R)-1-(Hydroxymethyl)-2-oxo-2-[(phenylmethyl)amino]ethyl]carbamic acid benzyl ester is utilized as a reagent in organic synthesis for the preparation of other chemicals. Its unique structure allows it to participate in various chemical reactions, facilitating the synthesis of a range of compounds.
Used in Pharmaceutical Research and Development:
N-[(1R)-1-(Hydroxymethyl)-2-oxo-2-[(phenylmethyl)amino]ethyl]carbamic acid benzyl ester may have potential applications in the pharmaceutical industry, where it could be explored for its properties and effects in drug development. Its specific chemical structure might offer opportunities for the creation of new therapeutic agents or the enhancement of existing ones.

Upstream product

• 6081-61-4 N-(benzyloxycarbonyl)-D-serine 
• 100-46-9 benzylamine 
• 501-53-1 benzyl chloroformate 
• 102988-98-7 C₁₆H₂₁NO₇ 

Downstream Products

• 196601-68-0 (R)-N-benzyl 2-N-(benzylcarboxycarbonyl)amino-3-methoxypropionamide 
• 196601-69-1 (R)-2-amino-N-benzyl-3-methoxypropanamide 
• 1219043-12-5 (R)-N-benzyl 2-N-(benzyloxycarbonyl)amino-3-(methoxy-d3)propionamide 
• 175481-36-4 lacosamide 
• 175481-38-6 Desmethyllacosamide 
• 175481-39-7 (2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide 

Relevant academic research and scientific papers

Application of Methyl Bisphosphine-Ligated Palladium Complexes for Low Pressure N-11C-Acetylation of Peptides

A mild and effective method is described for 11C-labeling of peptides selectively at the N-terminal nitrogen or at internal lysine positions. The presented method relies on the use of specific biphosphine palladium–methyl complexes and their high reactivity towards amino-carbonylation of amine groups in the presence [11C]carbon monoxide. The protocol facilitates the production of native N-11C-acetylated peptides, without any structural modifications and has been applied to a selection of bioactive peptides.

PROCESS FOR PREPARING (R)-2-ACETAMIDO-N-BENZYL-3-METHOXY-PROPIONAMIDE

Processes for preparing and purifying (R)-2-acetamido-N-benzyl-3-methoxy- propionamide of formula-1 and intermediates thereof are provided.

Primary amino acid derivatives: Compounds with anticonvulsant and neuropathic pain protection activities

Pharmacological management remains the primary method to treat epilepsy and neuropathic pain. We have advanced a novel class of anticonvulsants termed functionalized amino acids (FAAs). In this study, we examine FAA derivatives from which the terminal acetyl moiety was removed and termed these compounds primary amino acid derivatives (PAADs). Twenty-seven PAADs were prepared; the central C(2) R-substituent was varied, including C(2) stereochemistry, and the compounds were tested in rodent models of seizures and neuropathic pain. C(2)-Hydrocarbon N-benzylamide PAADs were potent anticonvulsants and excellent anticonvulsant activity (mice, ip; rat, po) was observed for C(2) R-substituted PAADs in which the R group was ethyl, isopropyl, or tert-butyl, and the C(2) stereochemistry conformed to the d-amino acid configuration ((R)-stereoisomer). These values surpassed the activities of several clinical antiepileptic drugs. The C(2) (R)-ethyl and C(2) (R)-isopropyl PAADs also displayed excellent activities in the mouse (ip) formalin neuropathic pain model. Significantly, unlike the FAA structure-activity relationship, PAAD anticonvulsant activity increased upon substitution of a methylene unit for a heteroatom in the R-substituent that was one atom removed from the C(2) site, suggesting that these PAADs function by a different pathway than FAAs.

PROCESS FOR PREPARING (R)-N-BENZYL-2-(BENYLOXYCARBONYLAMINO)-3-METHOXYPROPIONAMIDE

(R)—N-benzyl-2-(benzyloxycarbonylamino)-3-methoxypropionamide is an intermediate useful for preparing lacosamide. It can be prepared, for example, by combining (R)—N-benzyl-2-(benzyloxycarbonylamino)-3-hydroxypropionamide with dimethylsulfate, followed by mixing with an alkali or alkaline earth metal hydroxide at a temperature of about 25° C. to about ?15° C.

Lacosamide isothiocyanate-based agents: Novel agents to target and identify lacosamide receptors

(R)-Lacosamide ((R)-2, (R)-N-benzyl 2-acetamido-3-methoxypropionamide) has recently gained regulatory approval for the treatment of partial-onset seizures in adults.Whole animal pharmacological studies have documented that (R)-2 function is unique. A robust strategy is advanced for the discovery of interacting proteins associated with function and toxicity of (R)-2 through the use of (R)-2 analogues, 3, which contain "affinity bait (AB)" and "chemical reporter (CR)" functional groups. In 3, covalent modification of the interacting proteins proceeds at the AB moiety, and detection or isolation of the selectively captured protein occurs through the bioorthogonal CR group upon reaction with an appropriate probe. We report the synthesis, pharmacological evaluation, and interrogation of the mouse soluble brain proteome using 3 where the AB group is an isothiocyanate moiety. One compound, (R)-N-(4-isothiocyanato)benzyl 2-acetamido-3-(prop-2-ynyloxy) propionamide ((R)-9), exhibited excellent seizure protection in mice, and like (R)-2, anticonvulsant activity principally resided in the (R)-stereoisomer. Several proteins were preferentially labeled by (R)-9 compared with (S)-9, including collapsin response mediator protein 2. 2009 American Chemical Society.

Design and evaluation of affinity labels of functionalized amino acid anticonvulsants

Studies have shown that functionalized amino acids (FAA) exhibit outstanding activity in the maximal electroshock-induced seizure (MES) test in rodents. Affinity labels patterned in part after the potent antiepileptic (R)-N-benzyl-2-acetamido-3-methoxypropionamide ((R)-2) have been prepared as mechanistic probes to learn the pharmacological basis for FAA function. The chemical reactivity of the affinity labels with nucleophiles was assessed, and the labels were evaluated in in vitro radioligand assays and in the MES tests in rodents. The affinity labels did not bind to receptors known to effect seizure spread. Three affinity labels, (R,S)-N-benzyl-2-acetamido-6-isothiocyanatohexanamide ((R,S)-5), (R)-N-(4-isothiocyanatobenzyl)-2-acetamido-3-methoxypropionamide ((R)-6), and (R)-N-(3-isothiocyanatobenzyl)-2-acetamido-3-methoxy-propionamide ((R)-7), possessed excellent in vivo anticonvulsant activity and exhibited maximal activity at later time periods than typically observed for FAA. The anticonvulsant activity of 6 and 7 resided primarily in the (R)-enantiomer and the activity of (R)-6 and (R)-7 in rats (po) exceeded that of phenytoin. The chemical properties, pharmacological profile, and marked stereospecificity associated with 6 and 7 anticonvulsant activity make these compounds useful pharmacological tools for the study of the mode of action of FAA.

Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives

Efficient procedures for the synthesis of (R)-N-benzyl-2-amino-3- methoxypropionamide ((R)-3), 2-acetamido-3-methoxypropionic acid (4), and O- methylserine (5) are described beginning from (R)-Cbz-serine ((R)-7). The reactions proceeded with little or no racemization and permitted the synthesis of the potent anticonvulsant (R)N-benzyl-2-acetamido-3- methoxypropionamide ((R)-2). The anticonvulsant activities of 2-4 were determined revealing the surprising activity of (R)-2.