783300-35-6

Basic information

• Product Name: (S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID
• Synonyms: H-D-PHG(3-OME)-(C*CH2)OH;H-BETA-PHE(3-OME)-OH;RARECHEM LK HC T256;(S)-3-AMINO-3-(3-METHOXYPHENYL)PROPANOIC ACID;(S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID;Benzenepropanoic acid, beta-amino-3-methoxy-, (betaS)- (9CI);H-b-Phe(3-OMe)-OH;3'-Methoxy-beta-phenylalanine
• CAS NO: 783300-35-6
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.22
• Product Categories: METHOXY;3-Amino-3-phenylpropanoic Acid Analogs
• Mol File: 783300-35-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 350.2 °C at 760 mmHg
• Flash Point: 165.6 °C
• Appearance: /
• Density: 1.206 g/cm³
• Storage Temp.: 2-8°C
• PKA: 3.68±0.10(Predicted)
• CAS DataBase Reference: (S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID(783300-35-6)
• EPA Substance Registry System: (S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID(783300-35-6)

Safety Data

• Hazardous Substances Data: 783300-35-6(Hazardous Substances Data)

Usage

Description

(S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID, with the molecular formula C10H13NO3, is an amino acid derivative characterized by a 3-amino-3-(3-methoxyphenyl) propionic acid moiety. (S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID may hold significant potential in the pharmaceutical industry due to the importance of amino acids and their derivatives as fundamental building blocks in drug design and development.

Uses

Used in Pharmaceutical Industry:
(S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID is used as a building block for drug design and development due to its unique structure and the versatility of amino acid derivatives in creating novel therapeutic agents. Its potential applications may include the synthesis of new pharmaceutical compounds, the modification of existing drugs to improve their efficacy or reduce side effects, and the development of targeted drug delivery systems.
In the context of drug discovery and medicinal chemistry, (S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID could be utilized to:
1. Enhance the pharmacokinetic properties of drugs, such as absorption, distribution, metabolism, and excretion, by modifying the chemical structure of existing compounds.
2. Improve the pharmacodynamic effects of drugs by introducing functional groups that can interact with specific biological targets, such as enzymes, receptors, or ion channels.
3. Facilitate the development of prodrugs, which are biologically inactive compounds that are converted into active drugs within the body, potentially reducing side effects and improving drug safety.
4. Contribute to the creation of chiral drugs, where the stereochemistry of the compound can significantly impact its therapeutic effects and side effects.
While the specific applications of (S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID in the pharmaceutical industry may vary, its role as an amino acid derivative positions it as a valuable component in the ongoing pursuit of innovative and effective therapeutic agents.

Upstream product

• 951174-38-2 tert-butyl (R)-3-amino-3-(3-methoxyphenyl)propanoate 
• 181517-89-5 tert-butyl (S)-3-amino-3-(3-methoxyphenyl)propanoate 
• 21667-60-7 3-methoxybenzoylacetonitrile 
• 6099-04-3 3-methoxycinnamic acid 
• 181517-73-7 tert-butyl (E)-3-(3-methoxyphenyl)propenoate 
• 591-31-1 3-methoxy-benzaldehyde 
• 951174-30-4 tert-butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(3-methoxyphenyl)propanoate 
• 951174-20-2 tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(3-methoxyphenyl)propanoate 
• 100-83-4 meta-hydroxybenzaldehyde 
• 141-82-2 malonic acid 
• 15854-56-5 3-methoxy-cinnamic acid methyl ester 

Relevant articles and documents

The kinetic resolution of oxazinones by alcoholysis: access to orthogonally protected β-amino acids

The catalytic, alcoholytic kinetic resolution of oxazinones is reported. A novel, stereochemically dense cinchona alkaloid-based catalyst can facilitate the highly enantiodiscriminatory (Sup to 101) ring-opening of oxazinones equipped with electrophilic aryl units to generate orthogonally protected β-amino acids for the first time.

Characterization of a new nitrilase from Hoeflea phototrophica DFL-43 for a two-step one-pot synthesis of (S)-β-amino acids

A nitrilase from Hoeflea phototrophica DFL-43 (HpN) demonstrating excellent catalytic activity towards benzoylacetonitrile was identified from a nitrilase tool-box, which was developed previously in our laboratory for (R)-o-chloromandelic acid synthesis from o-chloromandelonitrile. The HpN was overexpressed in Escherichia coli BL21 (DE3), purified to homogeneity by nickel column affinity chromatography, and its biochemical properties were studied. The HpN was very stable at 30–40?°C, and highly active over a wide range of pH values (pH 6.0–10.0). In addition, the HpN could tolerate against several hydrophilic organic solvents. Steady-state kinetics indicated that HpN was highly active towards benzoylacetonitrile, giving a KM of 4.2?mM and a kcat of 170?s?1, the latter of which is ca. fivefold higher than the highest record reported so far. A cascade reaction for the synthesis of optically pure (S)-β-phenylalanine from benzoylacetonitrile was developed by coupling HpN with an ω-transaminase from Polaromonas sp. JS666 in toluene-water biphasic reaction system using β-alanine as an amino donor. Various (S)-β-amino acids could be produced from benzoylacetonitrile derivatives with moderate to high conversions (73–99%) and excellent enantioselectivity (> 99% ee). These results are significantly advantageous over previous studies, indicating a great potential of this cascade reaction for the practical synthesis of (S)-β-phenylalanine in the future.

Carica papaya lipase catalysed resolution of β-amino esters for the highly enantioselective synthesis of (S)-dapoxetine

An efficient synthesis of the (S)-3-amino-3-phenylpropanoic acid enantiomer has been achieved by Carica papaya lipase (CPL) catalysed enantioselective alcoholysis of the corresponding racemic N-protected 2,2,2-trifluoroethyl esters in an organic solvent. A high enantioselectivity (E > 200) was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. Based on the resolution of a series of amino acids, it was found that the structure of the substrate has a profound effect on the CPL-catalysed resolution. The enantioselectivity and reaction rate were significantly enhanced by switching the conventional methyl ester to an activated trifluoroethyl ester. When considering steric effects, the substituted phenyl and amino groups should not both be large for the CPL-catalysed resolution. The mechanism of the CPL-catalysed enantioselective alcoholoysis of the amino acids is discussed to delineate the substrate requirements for CPL-catalysed resolution. Finally, the reaction was scaled up, and the products were separated and obtained in good yields (≥ 80 %). The (S)-3-amino-3- phenylpropanoic acid obtained was used as a key chiral intermediate in the synthesis of (S)-dapoxetine with very high enantiomeric excess (> 99 %). A carica papaya lipase catalysed resolution of N-protected β-phenylalanine esters has been developed. High enantioselectivity was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. After 50 % conversion, the products were separated and used as key chiral intermediates for the synthesis of (S)-dapoxetine with > 99 % ee. Copyright