93964-79-5

Basic information

• Product Name: 2-amino-4-phenylbutyrate ethyl hydrochloride
• Synonyms: 2-Amino-4-phenylbutyrate ethyl hydrochloride; 2-Amino-4-phenylbutyrate ethyl HCl; ethyl 2-amino-4-phenyl-butanoate hydrochloride
• CAS NO: 93964-79-5
• Molecular Formula: C₁₂H₁₇NO₂*ClH
• Molecular Weight: 243.7298
• EINECS: 300-926-8
• Mol File: 93964-79-5.mol

Chemical Properties

• Boiling Point: 344.4°C at 760 mmHg
• Flash Point: 162.1°C
• Vapor Pressure: 4.67E-05mmHg at 25°C
• CAS DataBase Reference: 2-amino-4-phenylbutyrate ethyl hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-phenylbutyrate ethyl hydrochloride(93964-79-5)
• EPA Substance Registry System: 2-amino-4-phenylbutyrate ethyl hydrochloride(93964-79-5)

Safety Data

• Hazardous Substances Data: 93964-79-5(Hazardous Substances Data)

Usage

General Description

2-Amino-4-phenylbutyrate ethyl hydrochloride is a chemical compound that belongs to the category of amino acids. It is primarily used as an intermediate in the synthesis of pharmaceuticals and organic compounds. 2-Amino-4-phenylbutyrate ethyl hydrochloride is derived from ethyl ester and hydrochloride salt forms, and it is also known as N-phenethyl-4-aminobutyric acid ethyl ester hydrochloride. It has been studied for its potential applications in the medical field, particularly for its role in neurobiology and the central nervous system. Additionally, it has been investigated for its potential use as a drug precursor and in the production of various biochemicals.

Upstream product

• 5463-92-3 2-acetylamino-2-phenylethylmalonic acid diethyl ester 
• 17376-04-4 2-phenethyl iodide 
• 64-17-5 ethanol 
• 21176-60-3 2-(RS)-amino-4-phenylbutyric acid hydrochloride 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 422511-01-1 (RS)-homophenylalaninamide hydrochloride 
• 1316742-32-1 2-(RS)-(2-aminobenzoylamino)-4-phenylbutyric acid ethyl ester 
• 1316741-89-5 2-(RS)-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}-4-phenylbutyric acid ethyl ester 
• 1316741-97-5 (RS)-1H-indol-2-carboxylic acid 2-(1-hydroxycarbamoyl-3-phenylpropylcarbamoyl)phenylamide 
• 1316741-91-9 (RS)-1H-indole-2-carboxylic acid [2-(1-carbamoyl-3-phenylpropylcarbamoyl)phenyl]amide 
• 877078-66-5 (S)-ethyl 2-((S)-2-allylhexanamido)-4-phenylbutanoate 
• 877078-61-0 (S)-ethyl 2-((S)-2-isobutylpent-4-enamido)-4-phenylbutanoate 
• 1012-05-1 D,L-homophenylalanine 

Relevant articles and documents

In Situ-Generated Glycinyl Chloroaminals for a One-Pot Synthesis of Non-proteinogenic α-Amino Esters

An acetyl chloride-mediated cascade transformation involving a primary carbamate, ethyl glyoxylate, and various types of nucleophiles is reported for the synthesis of orthogonally protected α-amino esters. These reactions proceeded rapidly to afford the pivotal α-chloroglycine intermediate in excellent yields, which can be directly functionalized in situ with various types of nucleophiles. A mild and unique AcOH(cat.)/AcCl system was found to promote an autocatalytic-like condensation and facilitate the multicomponent assembly of non-proteinogenic α-amino esters. To better understand this one-pot transformation and the orchestration of the components' condensations, the investigation of a broader scope of nucleophiles and some kinetic studies are presented. Our findings suggest that the halogenation step toward the formation of α-chloroglycine is the rate-determining step likely proceeding through the formation of N-carbamoyl iminium. Also, the initial kinetic profiling for the nucleophilic substitution supports an SN1-like (SN2C+) mechanism in which nucleophiles add to the iminium-chloride tight ionic pair. These results lead ultimately to the design of a new protocol in which an achiral hydrogen bond donor thiourea catalyst was utilized to enhance the reaction scope and enable silylated nucleophiles to be efficiently exploited to synthesize novel non-proteinogenic α-amino esters.

New anthranilic acid based antagonists with high affinity and selectivity for the human cholecystokinin receptor 1 (hCCK1-R)

The anthranilic acid diamides represent the most recent class of nonpeptide CCK1 receptor (CCK1-R) antagonists. Herein we describe the second phase of the anthranilic acid C-terminal optimization using nonproteinogenic amino acids containing a phenyl ring in their side chain. The Homo-Phe derivative 2 (VL-0797) enhanced 12-fold the affinity for the rat CCK1-R affinity and 15-fold for the human CCK1-R relative to the reference compound 12 (VL-0395). The eutomer of 2 (6) exhibited a nanomolar range affinity toward the human CCK1-R and was at least 400-fold selective for the CCK1-R over the CCK2-R. Molecular docking in the modeled CCK1-R and its validation by site-directed mutagenesis experiments showed that the 6 binding site overlaps that occupied by the C-terminal bioactive region of the natural agonist CCK. Owing to their interesting properties, new compounds provided by this study represent a solid basis for further advances aimed at synthesis of clinically valuable CCK1-R antagonists.

Synthesis of [1-13C] and [1-15N] labelled DL-homophenylalanine via a key Neber rearrangement

A synthetic route involving a key Neber rearrangement is described for the preparation of both [1-13C] and [1-15N] DL-homophenylalanine (2- amino-4-phenylbutanoic acid), using suitably labelled sodium cyanide as the source of the isotopic label. These compounds have been prepared for use in studies on the biosynthesis of phenylethyl glucosinolate in Brassica napus. 3-Phenylpropanaldoxime, the initial biosynthetic product formed from homophenylalanine, was also prepared in 15N labelled form.

PHOSPHORUS CONTAINING COMPOUNDS AND USE AS HYPOTENSIVES

Phosphorus containing compounds of the formula STR1 wherein X is a substituted or unsubstituted imino or amino acid and A is STR2 These compounds possess angiotensin converting enzyme activity and are thus useful as hypertensive agents.