623950-02-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine is used as an intermediate in the synthesis of potential Dual delta-opioid antagonist/μ-opioid agonist for the treatment of diarrhea and irritable bowel syndrome. Its unique structure allows it to modulate opioid receptors, providing a targeted approach to managing these gastrointestinal conditions.

Upstream product

• 1227311-10-5 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-cyano-2,6-dimethylphenyl)propanoate 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 1206679-91-5 2,6-dimethyl-4-carbamoyl iodobenzene 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 80312-69-2 N-t-butoxycarbonyl-D,L-serinamide 
• 145235-85-4 methyl (Z)-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-2-propenoate 
• 137650-15-8 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoate 
• 623950-03-8 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2,6-dimethyl-4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate 
• 623950-04-9 4'-carboxyl N-Boc-2',6'-dimethyl-L-phenylalanine methyl ester 
• 623950-05-0 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-carbamoyl-2,6-dimethylphenyl)propanoate 

Downstream Products

• 623950-08-3 {1-(4-carbamoyl-2,6-dimethyl-benzyl)-2-oxo-2-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester 
• 623950-28-7 {1-(4-carbamoyl-2,6-dimethyl-benzyl)-2-oxo-2-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

L-alanine derivative preparation method

The invention relates to the preparation of pharmaceutical intermediates, and belongs to the field of organic synthesis, particularly to an L-alanine derivative preparation method, which comprises: carrying out a Negishi reaction on a compound 3 to obtain

PROCESS FOR THE PREPARATION OF OPIOID MODULATORS

It is described an industrially viable and advantageous process for the preparation of mixed μOR agonist/δOR antagonists (9). The invention also discloses the intermediates obtained in the process.

Preparation method of high-purity (S)-2-t-BOC-3-(4-carbamoyl-2, 6-dimethyl phenyl) propionic acid

The invention discloses a preparation method of high-purity (S)-2-t-BOC-3-(4-carbamoyl-2, 6-dimethyl phenyl) propionic acid (I) and pharmaceutically-acceptable salt thereof. The preparation method includes: using (R)-3-iodo-N-Boc-alaninate as a raw material, and synthesizing a compound (S)-2, 6-dimethyl-4-aminomethyl carbonyl-N-Boc-phenylalaninate (V) through two steps; subjecting the compound (V) to steps of Boc removal, extraction and purification and Boc loading sequentially to obtain a high-purity compound (V); hydrolyzing the high-purity compound (V) in an alkaline condition to obtain a compound I with purity higher than 99%. Compared with the prior art, the preparation method has the advantages that the compound V is purified through the steps of Boc removal, extraction and purification and Boc loading, and almost no byproduct is generated in the subsequent hydrolysis process, so that yield and purity of the compound I are improved, and the compound I has high application value.

Preparation method of eluxadoline intermediate compound

The invention provides a preparation method of an eluxadoline intermediate compound, and concretely discloses a method for preparing (S)-2-tertbutyloxycarbonyl amino-3-(4-carbamyl-2,6-dimethyl phenyl) propanoic acid shown by a formula 11. The method comprises the following steps of Step I, obtaining a compound shown by a formula 4 through a compound shown by a formula 1; Step II, obtaining a compound shown by a formula 5 by the compound shown by the formula 4; Step III, obtaining a compound shown by a formula 6 by the compound shown by the formula 5; Step IV, protecting amino groups in the compound shown by the formula 6 to obtain a compound shown by a formula 9; Step V, performing selective hydrolysis on the compound shown by the formula 9 to obtain a compound shown by a formula 10; then, performing ammonolysis to obtain the compound shown by the formula 11. The process routes of the method use the fire-new design; intermediate compounds obtained by the reaction in each step are all synthesized for the first time; a method of firstly performing carbonylation and then performing asymmetrical reduction is used in the process routes; the asymmetrical reduction is realized in the later stage; the catalyst consumption is favorably reduced; the cost is reduced. The formulas are shown as the accompanying drawing.

PROCESS FOR THE PREPARATION OF PROTECTED L-ALANINE DERIVATIVES

The present invention is directed to a novel process for the preparation of protected L-alanine derivatives, useful as intermediates in the synthesis of compounds useful as mu/delta opioid modulators.

PROCESS FOR THE PREPARATION OF OPIOID MODULATORS

The present invention is directed to novel processes for the preparation of opioid modulators (agonists and antagonists) and intermediates in their synthesis. The opioid modulators are useful for the treatment and prevention of as pain and gastrointestina

A convenient, large-scale synthesis of 4′-carboxamido N-Boc-2′,6′-dimethyl-l-phenylalanines

A large-scale synthesis of a series of 4′-carboxamido N-Boc-2′,6′-dimethyl-l-phenylalanines is described. This method features mild reaction conditions and high chemical yields from commercially available N-Boc-2′,6′-dimethyl-l-tyrosine methyl ester.

NOVEL COMPOUNDS AS OPIOID RECEPTOR MODULATORS

The present invention is directed to novel opioid receptor modulators of Formula (I). The invention further relates to methods for preparing such compounds, pharmaceutical compositions containing them, and their use in the treatment of disorders that may

Novel compounds as opioid receptor modulators

This invention is directed towards novel compounds as opioid receptor modulators, antagonists, and agonists useful for the treatment of opioid modulated disorders such as pain and gastrointestinal disorders.