614-19-7

Basic information

• Product Name: 3-Amino-3-phenylpropionic acid
• Synonyms: 2-Amino-2-phenylpropansαure;Benzenepropanoicacid,βamino-;Benzenepropanoicacid,β-amino-,(±)-;DL-3-Amino-3-phenylpropionsαure;DL-Aminohydrocinnamicacid;DL-β-Phe-OH;R,S-3-Amino-3-phenyl-propionicacid;β-Aminohydrocinnamicacid
• CAS NO: 614-19-7
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• EINECS: 210-371-2
• Product Categories: Benzene series;Amino Acids and Derivatives;Organic acids;B-Amino;Pyridines
• Mol File: 614-19-7.mol

Chemical Properties

• Melting Point: 222 °C (dec.)(lit.)
• Boiling Point: 293.03°C (rough estimate)
• Flash Point: 139.8 °C
• Appearance: white crystalline powder
• Density: 1.1603 (rough estimate)
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.45±0.12(Predicted)
• Water Solubility: SOLUBLE
• BRN: 2803286
• CAS DataBase Reference: 3-Amino-3-phenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-3-phenylpropionic acid(614-19-7)
• EPA Substance Registry System: 3-Amino-3-phenylpropionic acid(614-19-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25-37/39
• WGK Germany: 3
• Hazardous Substances Data: 614-19-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Amino-3-phenylpropionic acid is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows it to be incorporated into a wide range of drug molecules, enhancing their therapeutic properties.
Used in Platelet Aggregation Inhibitors:
3-Amino-3-phenylpropionic acid is used as a key component in the synthesis of platelet aggregation inhibitors. These inhibitors play a crucial role in preventing blood clot formation, which can lead to life-threatening conditions such as heart attacks and strokes.
Used in Human Gonadotropin-Releasing Hormone Receptor Antagonists:
3-Amino-3-phenylpropionic acid is also used as a reagent in the synthesis of human gonadotropin-releasing hormone (GnRH) receptor antagonists. These antagonists are important in the treatment of various hormonal disorders, including endometriosis, uterine fibroids, and certain types of cancer.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 27, p. 2223, 1979 DOI: 10.1248/cpb.27.2223

InChI:InChI=1/C9H11NO2/c10-8(6-9(11)12)7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)

Upstream product

• 112545-23-0 N-(R)-α-Methylbenzyl-(S)-3-phenylisoxazolidin-5-one 
• 161671-34-7 tert-butyl (R)-3-amino-3-phenylpropionate 
• 65451-19-6 N-(phenylacetyl)-3-amino-3-phenylpropanoic acid 
• 5661-55-2 4-phenylazetidin-2-one 
• 850011-53-9 3-formylamino-3-phenyl-propionic acid ethyl ester 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 63-91-2 L-phenylalanine 
• 40638-98-0 (R/S)-3-(acetylamino)-3-phenylpropanoic acid 
• 127001-34-7 N-Benzylidene<(R)-(-)-α-methylbenzyl>amine N-oxide 
• 135383-44-7 5-Chloro-3-phenyl-2-((R)-1-phenyl-ethyl)-isoxazolidine-5-carbonitrile 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 37088-67-8 methyl (3R)-3-amino-3-phenylpropanoate 
• 150-30-1 Phenylalanine 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 94099-69-1 (R)-3-dimethylamino-3-phenylpropionic acid 
• 263247-50-3 (R)-3-benzamido-3-phenylpropanoic acid 
• 100923-36-2 (R)-3-[4-((R)-2-Carboxy-1-phenyl-ethylcarbamoyl)-pyridine-2-sulfonylamino]-3-phenyl-propionic acid 
• 144494-74-6 (R)-3-benzamido-3-phenylpropanoic acid methyl ester 
• 36567-72-3 (S)-3-hydroxy-3-phenylpropanoic acid 
• 161024-80-2 (R)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid 
• 1050324-77-0 (R)-3-phenyl-3-(2,2,2-trifluoroacetamido)propanoic acid 
• 820223-49-2 (R)-{[4-(4-trifluoromthoxyphenyl)thien-2-yl]carboxamido}(phenyl)propanoic acid 
• 784205-11-4 C₁₆H₁₄F₃NO₄S 
• 784205-62-5 C₁₅H₁₃Cl₂NO₄S 

Relevant articles and documents

Preparation methods of beta-azido acid and beta-amino acid compounds and application thereof

The invention discloses a preparation method of beta-azido acid, which comprises the following step of: carrying out a reaction on an ethylene compound, CZ1Z2Z3Z4 and trimethylsilyl azide as initial raw materials to obtain the beta-azido acid. The ethylene compound has a structural general formula as shown in a formula I, and the beta-azido acid has a structural general formula as shown in a formula II, wherein R is selected from one of alkyl, substituted alkyl, heteroaryl and substituted heteroaryl; and Z1, Z2, Z3 and Z4 are respectively and independently at least one selected from fluorine, chlorine, bromine and iodine. The invention further provides beta-amino acid and application of the preparation method. The preparation methods of the beta-azido acid and the beta-amino acid, provided by the invention, have the advantages of cheap raw materials and catalysts, mild reaction conditions, simplicity in operation, high reaction efficiency and the like.

Glutamate as an Efficient Amine Donor for the Synthesis of Chiral β- and γ-Amino Acids Using Transaminase

A recyclable glutamate amine donor system employing transaminase (TA), glutamate dehydrogenase (GluDH) and mutant formate dehydrogenase (FDHm) was developed, wherein amine donor Glu was regenerated using GluDH and thereby circumvented the inhibition of TA by α-ketoglutarate. Various enantiopure β-, γ-amino acids, and amines were successfully synthesized with high conversions and excellent enantiomeric excess using this system.

Β-phenylalanine ester synthesis from stable β-keto ester substrate using engineered ω-transaminases

The successful synthesis of chiral amines from ketones using ω-transaminases has been shown in many cases in the last two decades. In contrast, the amination of β-keto acids is a special and relatively new challenge, as they decompose easily in aqueous solution. To avoid this, transamination of the more stable β-keto esters would be an interesting alternative. For this reason, ω-transaminases were tested in this study, which enabled the transamination of the β-keto ester substrate ethyl benzoylacetate. Therefore, a ω-transaminase library was screened using a coloring o-xylylenediamine assay. The ω-transaminase mutants 3FCR_4M and ATA117 11Rd show great potential for further engineering experiments aiming at the synthesis of chiral (S)- and (R)-β-phenylalanine esters. This alternative approach resulted in the conversion of 32% and 13% for the (S)- and (R)-enantiomer, respectively. Furthermore, the (S)-β-phenylalanine ethyl ester was isolated by performing a semi-preparative synthesis.

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.

Synthetic method for novel chiral ligand, metal chelate, multiple unnatural amino acids, maraviroc and key intermediate thereof

The invention discloses a synthetic method for a novel chiral ligand, a metal chelate, multiple unnatural amino acids, maraviroc and a key intermediate thereof. According to the synthetic method, (R)-2-methylproline is selected as a starting material, and asymmetrical resolution is induced by utilizing a nickel chelate, so that (S)-beta3-amino acid is obtained, and (S)-3-amino-3-phenylpropionic acid is taken as the key intermediate for synthesizing maraviroc, so that yield is high, and ee value reaches more than or equal to 98.2%. The method disclosed by the invention has the advantages that source of raw materials is wide, conditions of a synthetic process are mild, control is easy, and optical purity of products is high.

Configurationally Stable (S)- and (R)-α-Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected β3-Amino Acids

Reported herein is a chemical method for the direct resolution of unprotected racemic β-substituted-β-amino acids (β3-AAs) that uses specially designed, stable, and recyclable α-methylproline-derived chiral ligands. The versatility of this methodology is unmatched by biocatalytic approaches. The method shows a broad synthetic generality for various aryl- or alkyl-substituted β3-AAs, and the new nonracemizable ligands can be accessed readily. Furthermore, the presented method produces an excellent stereochemical outcome and has a fully recyclable source of chirality, and the reaction conditions are operationally simple and convenient. The procedure has also been successfully applied to the scalable synthesis of the anti-HIV drug maraviroc.

A process for preparing S or R-type optical isomer 3 - amino - 3 - phenyl propionic acid

The invention discloses a method for preparing an S or R type optical isomer 3-amino-3-phenyl propionic acid, wherein R or S represents a chiral center configuration. The method includes the steps: 1) preparing an S or R type optical isomer 3-amino-3-phenyl propionic acid camphor sulfonic acid double salt; 2) carrying out free hydrolysis; after carrying out acid or alkali free hydrolysis of the S or R type optical isomer 3-amino-3-phenyl propionic acid camphor sulfonic acid double salt, filtering to obtain the S or R type optical isomer 3-amino-3-phenyl propionic acid. Used raw material and a split reagent are low in price and easy to obtain, a chiral induction body can be used repeatedly, three wastes are few, moreover, the three processes are greatly simplified, and the method can simultaneously obtain the S or R type optical isomer compound, and is low in cost and suitable for industrialized production.

Chiral synthesis method for chiral beta-amino acid and synthesis method for medicinal intermediate

The invention relates to a chiral synthesis method for chiral beta-amino acid. The chiral synthesis method comprises the following steps: reacting a compound shown in formula (II) with an acylation reagent to prepare anhydride intermediate reaction liquid under the action of alkali; adding Meldrum's acid into the anhydride intermediate reaction liquid, and performing reaction to generate a compound shown in formula (III); reacting the compound shown in formula (III) with a compound shown in formula (IV) to generate a compound shown in formula (V); reducing the compound shown in formula (V) to generate a compound shown in formula (VI); performing acidic hydrolysis on the compound shown in formula (VI) to generate a compound shown in formula (I), i.e., the chiral beta-amino acid. The chiral synthesis method has the advantages of convenience for synthesis, low cost and simple process, and compared with a disclosed preparation method, is more suitable for industrial production.

Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts

An enzymatic strategy for the preparation of (R)-β-arylalanines employing phenylalanine aminomutase and ammonia lyase (PAM and PAL) enzymes has been demonstrated. Candidate PAMs with the desired (S)-selectivity from Streptomyces maritimus (EncP) and Bacillus sp. (PabH) were identified via sequence analysis using a well-studied template sequence. The newly discovered PabH could be linked to the first ever proposed biosynthesis of pyloricidin-like secondary metabolites and was shown to display better β-lyase activity in many cases. In spite of this, a method combining the higher conversion of EncP with a strict α-lyase from Anabaena variabilis (AvPAL) was found to be more amenable, allowing kinetic resolution of five racemic substrates and a preparative-scale reaction with >98% (R) enantiomeric excess. This work represents an improved and enantiocomplementary method to existing biocatalytic strategies, allowing simple product separation and modular telescopic combination with a preceding chemical step using an achiral aldehyde as starting material. (Figure presented.).

A chiral analog of the bicyclic guanidine TBD: Synthesis, structure and Br?nsted base catalysis

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