623950-05-0

Basic information

• Product Name: 4'-carbamoyl N-Boc-2',6'-dimethyl-L-phenylalanine methyl ester
• Synonyms: 4'-carbamoyl N-Boc-2',6'-dimethyl-L-phenylalanine methyl ester;L-Phenylalanine, 4-(aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-, methyl ester;methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-carbamoyl-2,6-dimethylphenyl)propanoate;(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-carbamoyl-2,6-dimethylphenyl)propanoate
• CAS NO: 623950-05-0
• Molecular Formula: C₁₈H₂₆N₂O₅
• Molecular Weight: 350.40944
• EINECS: -0
• Mol File: 623950-05-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4'-carbamoyl N-Boc-2',6'-dimethyl-L-phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-carbamoyl N-Boc-2',6'-dimethyl-L-phenylalanine methyl ester(623950-05-0)
• EPA Substance Registry System: 4'-carbamoyl N-Boc-2',6'-dimethyl-L-phenylalanine methyl ester(623950-05-0)

Safety Data

• Hazardous Substances Data: 623950-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4'-carbamoyl N-Boc-2',6'-dimethyl-L-phenylalanine methyl ester is used as an impurity in the production of Eluxadoline (E508195), an orally-active drug. The application reason is that it is a byproduct in the synthesis process of Eluxadoline, which is utilized to alleviate symptoms of irritable bowel syndrome, such as diarrhea and abdominal pain.

Upstream product

• 112766-18-4 methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate 
• 298693-79-5 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoate 
• 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 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1206679-91-5 2,6-dimethyl-4-carbamoyl iodobenzene 
• 1048677-12-8 benzyl 4-iodo-3,5-dimethylbenzoate 
• 1048677-11-7 4-iodo-3,5-dimethylbenzoic acid 
• 623950-03-8 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2,6-dimethyl-4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 76757-90-9 N-(tert-butoxycarbonyl)-D-tyrosine methyl ester 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 864825-84-3 (Z)-2-tert-Butoxycarbonylamino-3-(4-carbamoyl-2,6-dimethyl-phenyl)acrylic acid methyl ester 
• 137650-15-8 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoate 

Downstream Products

• 623950-02-7 (S)-2-((tert-butoxycarbonyl)amino)-3-(4-carbamoyl-2,6-dimethylphenyl)propanoic acid 

Relevant articles and documents

Novel method for preparing iludoline intermediate

The invention discloses a preparation method of a pharmaceutical intermediate, 4-(aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine methyl ester, for treating irritable bowel syndrome (IBS-D). The preparation method comprises the following steps: with 4-iodine-3,5-dimethyl benzoic acid as a raw material, protecting carboxyl through a group, carrying out Negishi couplingreaction under the catalysis of Pd2(dba)3, removing the carboxyl protecting group, and forming active ester to react with ammonia water, thereby obtaining the product. The invention provides a novel synthetic route for a drug intermediate for treating irritable bowel syndrome (IBS-D); the reaction conditions are easy to control, the post-treatment operation is simple, and industrial production canbe smoothly realized.

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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.

Method for preparing alanine derivative

The invention discloses a method for preparing an alanine derivative represented by a formula (I) shown in the description. The alanine derivative can serve as synthesis intermediates of opium receptor regulators, such as a synthesis intermediate of eluxadoline. According to the method, chiral tyrosine which is cheap and readily available serves as an initial raw material, a bran-new synthesis route for preparing the alanine derivative is provided, the total yield of the entire reaction route is high, the cost is low, the reaction conditions are mild, and the operation is simple and safe, so that the method is applicable to large-scale industrial production.

Preparation method of alanine derivatives

The invention discloses a method for preparing alanine derivatives disclosed as Formula (I). The alanine derivatives can be used as a synthesis intermediate of an opioid receptor regulator, such as a synthesis intermediate of eluxadoline. By using the cheap and accessible chiral tyrosine as the initial raw material, the invention provides a brand-new synthesis route for preparing alanine derivatives. The whole reaction route has the advantages of high total yield, low cost and mild reaction conditions, is simple and safe for operation, and is suitable for large-scale industrial production.

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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

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

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.