103123-51-9

Basic information

• Product Name: (S)-Methyl 3-((S)-1-phenylethylaMino)butanoate
• Synonyms: (S)-Methyl 3-((S)-1-phenylethylaMino)butanoate
• CAS NO: 103123-51-9
• Molecular Formula: C₁₃H₁₉NO₂
• Molecular Weight: 221.29546
• Mol File: 103123-51-9.mol

Chemical Properties

• Boiling Point: 306.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.014±0.06 g/cm3(Predicted)
• PKA: 8.03±0.29(Predicted)
• CAS DataBase Reference: (S)-Methyl 3-((S)-1-phenylethylaMino)butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Methyl 3-((S)-1-phenylethylaMino)butanoate(103123-51-9)
• EPA Substance Registry System: (S)-Methyl 3-((S)-1-phenylethylaMino)butanoate(103123-51-9)

Safety Data

• Hazardous Substances Data: 103123-51-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Methyl 3-((S)-1-phenylethylaMino)butanoate is used as a key intermediate in the synthesis of pharmaceuticals for the treatment of central nervous system conditions such as depression, anxiety, and schizophrenia. Its role in drug production is crucial due to its structural similarity to phenylalanine, which allows for the development of targeted therapies.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-Methyl 3-((S)-1-phenylethylaMino)butanoate is utilized as a component in the development of various agrochemical products. Its specific application reasons in this industry are not provided in the materials, but it is likely due to its ability to be incorporated into molecules with biological activity relevant to agriculture.
Used in Biotechnology:
(S)-Methyl 3-((S)-1-phenylethylaMino)butanoate is also used in the field of biotechnology, where it may serve as a building block for the creation of novel bioactive molecules or be involved in the development of new biological processes. The exact application reasons in biotechnology are not detailed in the provided materials, but the compound's importance in drug production suggests potential for similar utility in biotechnological applications.

Upstream product

• 623-43-8 crotonic acid methyl ester 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 115914-08-4 (S)-N-(1-phenylethyl)prop-2-en-1-amine 
• 3129-98-4 (S)-N-benzylidene(1-phenylethylamine) 
• 17480-69-2 (S)-N-benzyl-1-phenylethylamine 
• 67-56-1 methanol 
• 164660-11-1 tert-butyl (3S,αS)-3-[N-(α-methylbenzyl)amino]butanoate 
• 623-43-8 methyl crotonate 
• 618-36-0 rac-methylbenzylamine 

Downstream Products

• 1257532-06-1 3-(4-chlorophenyl)-6-(S)-methyl-1-[(S)-1-phenylethyl]-2-thioxotetrahydropyrimidin-4(1H)-one 
• 1257532-02-7 3-(3-chloro-4-fluorophenyl)-6-(S)-methyl-1-[(S)-1-phenylethyl]-2-thioxotetrahydropyrimidin-4(1H)-one 
• 1257531-87-5 3-(3-chloro-4-cyanophenyl)-6-(S)-methyl-1-[(S)-1-phenylethyl]-2-thioxotetrahydropyrimidin-4(1H)-one 
• 1420778-20-6 3-(4-chloro-3-(trifluoromethyl)phenyl)-6-(S)-methyl-1-[(S)-1-phenylethyl]-2-thioxotetrahydropyrimidin-4(1H)-one 
• 26757-80-2 (1¹S,4S)-4-methyl-1-(α-methylbenzyl)azetidin-2-one 
• 6078-06-4 (S)-methyl 3-aminobutanoate 
• 6078-06-4 (R)-methyl 3-aminobutanoate hydrochloride 

Relevant articles and documents

Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations

Abstract A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with and without 1-substitution, is described; no N-protective group is required. A related regioselective Dieckmann cyclisation is also described that uses Davies' α-methylbenzylamine auxiliary and affords 6-substituted piperidine-2,4-diones enantioselectively.

Design and synthesis of optically pure 3-aryl-6-methyl-2- thioxotetrahydropyrimidin-4(1H)-ones as anti-prostate cancer agents

3-Aryl-6-methyl-2-thioxotetrahydropyrimidin-4(1H)-ones were proposed as a new class of anti-prostate cancer agents on the basis of molecular modeling studies. Stereoselective synthesis of 3-aryl-6-methyl-2- thioxotetrahydropyrimidin-4(1H)-one derivatives was achieved by chiral induction employing (R)/(S)-α-methyl benzylamine and subsequent debenzylation with HBr in AcOH afforded the desired enantiomers in good yields. The compounds were screened in vitro against prostate cancer cell lines, PC-3 and LNCaP and the most potent derivatives were identified. the Partner Organisations 2014.

Design and synthesis of optically pure 3-aryl-6-methyl-2-thioxotetrahydropyrimidin-4(1H)-ones as anti-prostate cancer agents

3-Aryl-6-methyl-2-thioxotetrahydropyrimidin-4(1H)-ones were proposed as a new class of anti-prostate cancer agents on the basis of molecular modeling studies. Stereoselective synthesis of 3-aryl-6-methyl-2-thioxotetrahydropyrimidin-4(1H)-one derivatives was achieved by chiral induction employing (R)/(S)-α-methyl benzylamine and subsequent debenzylation with HBr in AcOH afforded the desired enantiomers in good yields. The compounds were screened in vitro against prostate cancer cell lines, PC-3 and LNCaP and the most potent derivatives were identified. This journal is

Michael additions of amines to methyl acrylates promoted by microwave irradiation

A simple and efficient protocol has been developed for the Michael addition of amines to α,β-unsaturated esters under microwave irradiation. Under these conditions there was a significant decrease in the reaction time, increases in the yields and increased purity of the products.

Lithium (α-Methylbenzyl)allylamide: A Differentially Protected Chiral Ammonia Equivalent for the Asymmetric Synthesis of β-Amino Acids and β-Lactams

The addition products from the highly stereoselective conjugate additions of lithium (αS)-(α-methylbenzyl)allylamide to α,β-unsaturated tert-butyl esters are efficiently deallylated with tris(triphenylphosphine)rhodium(I) chloride and converted, after tra

Enantioselective Synthesis of β-Amino Acids. 5. Stereoselective Reaction of Chiral Pyrimidinone Enolates with Aldehydes

Hydro-pyrimidinones ((2S,6R)-3) and ((2S)-6) were prepared from methyl crotonate via 3-aminobutanoate, and their corresponding lithium enolate and dienolate derivatives were added to various aldehydes.The high regio- and stereoselectivities observed in these aldol reactions pave the road for the preparation of enantiomerically pure β-hydroxy-β'-amino acids.The structures of the products were confirmed by X-ray crystal structure analysis (eight examples).

194. Diastereoselecktive Alkylation of 3-Aminobutanoic Acid in the 2-Position

The enantiomerically pure 3-aminobutanoic acids (R)- and (S)-6 are readily available by preparative HPLC separation of the two diastereoisomers 5 obtained from addition of (S)-phenethylamine to methyl crotonate and subsequent hydrogenolysis (Scheme 2). (S)-methyl 3-(benzoylamino)butanoate ((S)-3) is also available by enzymatic kinetic resolution with pig-liver esterase.The N-benzoyl- and N-benzyloxycarbonyl derivatives rac-3, 8,and 9 of 3-aminobutanoates are doubly deprotonated with LDA and alkylated or aminated in high selectivity (17 examples, relative topicity like; see Tables 1 and 2).The configuration of three of the products is assigned (Schemes 4-6), and in four cases, the free α-substituted β-amino acid is prepared by acidic hydrolysis (see Table 3).It is shown that the doubly lithiated β-amino-acid derivative is solubilized, and its reactivity may be strongly influenced by the presence of 3 equiv. of LiCl.

α-ALKYLATION OF β-AMINOBUTANOATES WITH lk-1,2-INDUCTION

Dilithiated methyl- or ethyl-N-benzoyl-3-aminobutanoates are alkylated or added to benzaldehyde to give products of l- and u,u-configuration respectively.Several methods are presented by which enantiomerically pure 3-aminobutanoic derivatives can be prepared.