177966-65-3

Usage

Uses

Used in Pharmaceutical Synthesis:
METHYL (3S)-3-AMINO-3-(4-HYDROXYPHENYL)PROPANOATE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and organic compounds.
Used in Drug Development:
In the field of drug development, METHYL (3S)-3-AMINO-3-(4-HYDROXYPHENYL)PROPANOATE is utilized as a building block for creating novel therapeutic agents, thanks to its unique structural features and potential biological activity.
Used in Medicinal Chemistry:
METHYL (3S)-3-AMINO-3-(4-HYDROXYPHENYL)PROPANOATE is employed in medicinal chemistry as a compound of interest for further research, given its potential to be integrated into the design and synthesis of new pharmaceutical entities.
Used in Biological Research:
Due to its potential biological activity, METHYL (3S)-3-AMINO-3-(4-HYDROXYPHENYL)PROPANOATE may also be used in biological research to explore its effects and interactions within biological systems, which could lead to new insights and applications in the pharmaceutical industry.

Upstream product

• 67-56-1 methanol 
• 152786-27-1 (S)-3-amino-3-(4-hydroxyphenyl)propanoic acid 
• 84184-51-0 (E)-methyl 3-(4-(benzyloxy)phenyl)acrylate 
• 134430-95-8 methyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-benzyloxyphenyl)propanoate 

Downstream Products

• 474295-85-7 methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoate 
• 1325688-50-3 (3S)-(2-azido-acetylamino)-3-(4-hydroxy-phenyl)propionic acid methyl ester 
• 444646-39-3 [1-(4-dimethylcarbamoyloxy-phenyl)-3-(4-nitro-phenoxy)-propyl]-methyl-carbamic acid tert-butyl ester 
• 474295-88-0 [1-(4-dimethylcarbamoyloxy-phenyl)-3-(4-nitro-phenoxy)-propyl]-carbamic acid tert-butyl ester 
• 474295-86-8 3-tert-butoxycarbonylamino-3-(4-dimethylcarbamoyloxy-phenyl)-propionic acid methyl ester 
• 474295-87-9 t-butyl (S)-[1-[(4-dimethylcarbamoyloxy)phenyl]-3-hydroxypropyl]carbamate 
• 54732-46-6 (S)-β-tyrosine hydrochloride 

Relevant academic research and scientific papers

Design, Synthesis, and Structure-Activity Relationship Studies of (4-Alkoxyphenyl)glycinamides and Bioisosteric 1,3,4-Oxadiazoles as GPR88 Agonists

Increasing evidence implicates the orphan G protein-coupled receptor 88 (GPR88) in a number of striatal-associated disorders. In this study, we report the design and synthesis of a series of novel (4-alkoxyphenyl)glycinamides (e.g., 31) and the corresponding 1,3,4-oxadiazole bioisosteres derived from the 2-AMPP scaffold (1) as GPR88 agonists. The 5-amino-1,3,4-oxadiazole derivatives (84, 88-90) had significantly improved potency and lower lipophilicity compared to 2-AMPP. Compound 84 had an EC50 of 59 nM in the GPR88 overexpressing cell-based cAMP assay. In addition, 84 had an EC50 of 942 nM in the [35S]GTPγS binding assay using mouse striatal membranes but was inactive in membranes from GPR88 knockout mice, even at a concentration of 100 μM. In vivo pharmacokinetic testing of 90 in rats revealed that the 5-amino-1,3,4-oxadiazole analogues may have limited brain permeability. Taken together, these results provide the basis for further optimization to develop a suitable agonist to probe GPR88 functions in the brain.

Homochiral lithium amides for the asymmetric synthesis of β-amino acids

Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α,β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid, (R)-β-amino pentanoic acid, (S)-β-leucine, (R)-β-amino octanoic acid, (S)-β-phenylalanine, (S)-β-tyrosine methyl ether, (S)-β-tyrosine hydrochloride and (S)-β-(2-methoxyphenyl)-β-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-β-DOPA and (R)-β-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral β-amino esters is also delineated.

BENZYLAMINE ANALOGUE

A compound of the formula (I): [wherein R1 represents a C1-C6 alkyl group etc., R2 and R3 are the same or different and represent a hydrogen atom etc., Ra represents a C1-C6 alkyl group etc., Arom represents an aryl group etc., A represents a C1-C6 alkylene group, E represents a single bond, an oxygen atom, a sulfur atom etc., X1 and X2 are the same or different and represent an oxygen atom or a sulfur atom] or a pharmacologically acceptable salt or ester thereof.

ASYMMETRIC SYNTHESIS OF R-β-AMINO BUTANOIC ACID AND S-β-TYROSINE: HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO α,β-UNSATURATED ESTERS.

Michael addition of the lithium amide derived from R-N-(α-methylbenzyl)benzylamine to benzyl E-crotonate is highly stereoselective (95percent d.e.) giving after debenzylation and crystallisation homochiral R-β-amino butanoic acid.A similar addition to methyl E-(p-benzyloxy)cinnamate is completely stereoselective giving after debenzylation and acid hydrolysis homochiral S-β-tyrosine as its HCl salt.