3082-69-7

Basic information

• Product Name: (S)-3-Amino-3-phenylpropionicacid,ethylester
• Synonyms: (S)-3-Amino-3-phenylpropionicacid,ethylester;(S)-3-Amino-3-phenylpropanoic acid ethyl ester;(S)-3-Phenyl-3-aminopropionic acid ethyl ester;(S)-β-Aminobenzenepropanoic acid ethyl ester;[S,(-)]-β-Aminohydrocinnamic acid ethyl ester;Ethyl (S)-3-aMino-3-phenylpropanoate
• CAS NO: 3082-69-7
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• Product Categories: Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 3082-69-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 140-150 °C(Press: 16 Torr)
• Appearance: /
• Density: 1.075±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 7.75±0.10(Predicted)
• CAS DataBase Reference: (S)-3-Amino-3-phenylpropionicacid,ethylester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Amino-3-phenylpropionicacid,ethylester(3082-69-7)
• EPA Substance Registry System: (S)-3-Amino-3-phenylpropionicacid,ethylester(3082-69-7)

Safety Data

• Hazardous Substances Data: 3082-69-7(Hazardous Substances Data)

Usage

Description

(S)-3-Amino-3-phenylpropionic acid, ethyl ester, also known as (βS)-β-Aminobenzenepropanoic acid ethyl ester, is an organic compound with the molecular formula C11H13NO2. It is a derivative of amino acids and possesses a phenyl group attached to the propionic acid backbone. (S)-3-Amino-3-phenylpropionicacid,ethylester is characterized by its potential reactivity and structural diversity, making it a versatile building block in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
(S)-3-Amino-3-phenylpropionic acid, ethyl ester is used as a key intermediate in the synthesis of CCR5 antagonists, which are crucial in the treatment of HIV. These antagonists block the CCR5 co-receptor, preventing the HIV virus from entering human cells and thus inhibiting the viral replication process.
Additionally, (S)-3-Amino-3-phenylpropionic acid, ethyl ester is used in the preparation of 1,4-Benzoxazin-3(4H)-one derivatives. These derivatives exhibit antithrombotic activity, which means they can help in preventing blood clot formation. This property makes them valuable in the development of medications for the treatment and management of conditions associated with thrombosis, such as deep vein thrombosis, pulmonary embolism, and myocardial infarction.

Upstream product

• 42201-84-3 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 
• 253665-35-9 (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide 
• 884318-81-4 (R)-ethyl 3-(N-benzyl-N-((R)-1-phenylethyl)amino)-3-phenylpropanoate 
• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 4192-77-2 ethyl cinnamate 
• 100-52-7 benzaldehyde 
• 650601-35-7 ethyl 3-amino-3-phenylacrylate methanesulfonate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1169704-19-1 (S)-ethyl 3-((R)-1,1-dimethylethylsulfinamido)-3-phenylpropanoate 
• 342626-64-6 ethyl 3-(methoxyimino)-3-phenylpropanoate 
• 33831-72-0 ethyl 3-amino-3-phenylprop-2-enoate 
• 64-17-5 ethanol 
• 83649-47-2 (S)-(-)-β-Phenyl-β-alanine hydrochloride 

Downstream Products

• 56613-80-0 D-2-phenylglycinol 
• 621-82-9 Cinnamic acid 
• 457059-32-4 ethyl (S)-3-((S)-2-(4,4-bis(trifluoromethyl)-3-(4-(3-(2-methylphenyl)ureido)-3-methoxybenzyl)-2,5-dioxoimidazolidin-1-yl)-2-(cyclopropylmethyl)acetylamino)-3-phenylpropionate 
• 295365-26-3 (2S)-2-phenyl-6-methyl-1,2,3,4-tetrahydropyridine-4-one 
• 295365-27-4 (2S)-2-phenyl-6-propyl-1,2,3,4-tetrahydropiridine-4-one 
• 295365-23-0 (2S)-2-phenyl-6-methyl-4-oxo-1,2,3,4-tetrahydropyridine-5-carboxylic acid ethyl ester 
• 295365-24-1 (2S)-2-phenyl-6-propyl-4-oxo-1,2,3,4-tetrahydropyridine-5-carboxylic acid ethyl ester 
• 101350-70-3 N-((R)-2-isocyanato-1-phenyl-ethyl)-benzamide 
• 62779-69-5 (R)-1,2-Diamino-1-phenylethane 
• 40639-03-0 (S)-3-benzoylamino-3-phenyl-propionic acid amide 
• 27129-49-3 (R)-4-phenyl-imidazolidin-2-one 
• 854689-14-8 salt of (S)-2-benzyloxycarbonylaminobutyric acid and (S)-3-amino-3-phenylpropionic acid ethyl ester 
• 854689-13-7 salt of (S)-benzyloxycarbonylvaline and (S)-3-amino-3-phenylpropionic acid ethyl ester 
• 167834-23-3 ethyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoate 

Relevant articles and documents

Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry

A Cu-catalyzed enantioselective hydroamination of α,β-unsaturated carbonyl compounds for the synthesis of β-amino acid derivatives was achieved through ligand-controlled reversal of the hydrocupration regioselectivity. While the hydrocupration of α,β-unsaturated carbonyl compounds to form α-cuprated species has been extensively investigated, we report herein that, in the presence of an appropriate ancillary chiral ligand, the opposite regiochemistry can be observed for cinnamic acid derivatives, leading to the delivery of the copper to the β-position. This copper can react with an electrophilic aminating reagent, 1,2-benzisoxazole, to provide enantioenriched β-amino acid derivatives, which are important building blocks for the synthesis of natural products and bioactive small molecules.

Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane

Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.

Scalable scny BRAnthesis of β-amino esters via reformatskcny BRA reaction with N-tert-butanesulfincny BRAl imines

The Reformatskcny BRA reagents derived from ethcny BRAl bromoacetate and tert-butcny BRAl bromoacetate add cleanlcny BRA, in high cny BRAield, and with good diastereoselectivitcny BRA to N-tert-butanesulfincny BRAl aldimines and ketimines. Importantlcny BRA, this reaction scales well (>50 mmol), and affords products upwards of 70% cny BRAield over three steps, starting from commerciallcny BRA available N-tert-butanesulfinamide, aldehcny BRAdes, and ketones.