Methyl 3-amino-3-phenylpropanoate

• CAS: 14898-52-3
• Catalog Number: ACM14898523
• Category: Main Products
• Molecular Weight: 179.21572
• Molecular Formula: C₁₀H₁₃NO₂
• Synonyms: methyl 3-amino-3-phenylpropanoate;Benzenepropanoic acid, b-aMino-, Methyl ester;Methyl3-aMino-3-phehylpropanoate;Benzenepropanoic acid, β-amino-, methyl ester

Case Study

Total Synthesis of 13-Hydroxyisobenzylamine Alkaloids Using Methyl 3-Amino-3-phenylpropionate

Li, Yi, et al. Helvetica chimica acta, 2003, 86(3), 579-591.

A convergent total synthesis of 13-hydroxyisocyclocelabenzine was achieved utilizing (3S)-methyl 3-amino-3-phenylpropanoate (4) as a chiral building block. The target C(13) epimers, 3a and 3b, resulting from macrocyclization, were isolated through repeated flash chromatography.
Synthetic Procedure Starting from Methyl (3S)-3-amino-3-phenylpropionate (4)
· Synthesis of Methyl (βS)-β-{{2-[2-(2-Cyanoethyl)-1,2,3,4-tetrahydro-4-hydroxy-1-oxoisoquinolin-4-yl]ethyl}amino}benzenepropanoate (11): A solution of (3S)-methyl 3-amino-3-phenylpropanoate (4) (0.316 g, 1.76 mmol) in dry methanol (15 mL) was treated with 3,4-dihydro-4-hydroxyisoquinolin-1(2H)-one derivative (5) HCl/methanol (0.71 mL, 3.53 mmol), followed by the addition of compound 5 (0.455 g, 1.76 mmol) and NaBH3CN (0.138 g, 2.20 mmol). The mixture was stirred at room temperature for 12 hours. After evaporation, the resultant residue was purified via chromatography (CH2Cl2/MeOH 30:1), yielding 11 (0.564 g, 75%).
· Synthesis of Methyl (βS)-β-{{2-[2-(3-Aminopropyl)-1,2,3,4-tetrahydro-4-hydroxy-1-oxoisoquinolin-4-yl]ethyl}amino}-benzenepropanoate (12): A solution of 11 (0.535 g, 1.27 mmol) in ethanol was combined with a 32% aqueous HCl solution (0.32 g, 2.81 mmol) and PtO2 (0.100 g). Hydrogenation was performed at room temperature under 50 psi of hydrogen for 6 hours, followed by filtration through Celite. The residue was purified by chromatography (CH2Cl2/MeOH/25% aq. NH4OH 90:10:1), yielding 12 (0.471 g, 87%).
· Synthesis of (+)-(9S,13R)- and (+)-(9S,13S)-13-Hydroxyisocyclocelabenzine: The target C(13) diastereomers 3a / 3b (185 mg, 60%) were obtained by macrocyclization from compound 12.

Enzymatic Kinetic Resolution of Methyl 3-Amino-3-Phenylpropionate as a Model Substrate

Rodríguez-Mata, María, et al. Advanced Synthesis & Catalysis, 2010, 352(2-3), 395-406.

Several optically active 3-amino-3-arylpropionic acid derivatives were prepared by stereoselective chemoenzymatic methods. Among them, methyl 3-amino-3-phenylpropionate (4a) was used as a model substrate for the kinetic resolution of β-amino esters.
The preferred resolution method was PCL-catalyzed partial hydrolysis of the ester. In this way, the corresponding (S)-3-amino-3-arylpropionic acids and methyl (R)-esters were obtained with very high enantioselectivity, which is reasonable in fragment-based methods. Therefore, the optimal binding position and conformation of the benzene ring and β-aminopropionate core, respectively, perfectly match the fast-reacting (S)-configuration of methyl (±)-3-amino-3-phenylpropionate.
Typical Procedure for the Enzymatic Hydrolysis of β-Amino Esters 4a-k
One solution of -amino ester 4a-k (0.28 mmol) in 1,4-dioxane (2.8 mL) was diluted with distilled water (25 mL, 1.40 mmol) and PCL (2:1 weight ratio to -amino ester). The mix was shaken around at 45°C and 250 rpm. The rate of the reaction - as measured by the enantiomeric excess of the -amino ester - was tracked via HPLC. The β-amino acid that formed in the reaction was removed and the amino ester left in solution was concentrated by evaporated organic solvent at reduced pressure. The following processes were performed in order to determine the enantiomeric excesses: a) β-amino ester was converted into methoxyacetamide (R)-5b, c, h-k or benzyl carbamate (R)-6a, d-g; b) β-amino acid was esterified and then converted into its related methoxyacetamide (S)-5b, c, h-k or benzyl carbamate (S)-6a, d-g.

Custom Q&A

What is the molecular formula of methyl 3-amino-3-phenylpropanoate?

The molecular formula of methyl 3-amino-3-phenylpropanoate is C10H13NO2.

What are the synonyms of methyl 3-amino-3-phenylpropanoate?

The synonyms of methyl 3-amino-3-phenylpropanoate are 3-Amino-3-phenyl-propionic acid methyl ester, methyl 3-amino-3-phenylpropionate, and methyl 3-amino-3-phehylpropanoate.

What is the molecular weight of methyl 3-amino-3-phenylpropanoate?

The molecular weight of methyl 3-amino-3-phenylpropanoate is 179.22 g/mol.

When was methyl 3-amino-3-phenylpropanoate created?

Methyl 3-amino-3-phenylpropanoate was created on July 19, 2005.

When was methyl 3-amino-3-phenylpropanoate last modified?

Methyl 3-amino-3-phenylpropanoate was last modified on October 21, 2023.

What is the IUPAC name of methyl 3-amino-3-phenylpropanoate?

The IUPAC name of methyl 3-amino-3-phenylpropanoate is methyl 3-amino-3-phenylpropanoate.

What is the InChI of methyl 3-amino-3-phenylpropanoate?

The InChI of methyl 3-amino-3-phenylpropanoate is InChI=1S/C10H13NO2/c1-13-10(12)7-9(11)8-5-3-2-4-6-8/h2-6,9H,7,11H2,1H3.

What is the InChIKey of methyl 3-amino-3-phenylpropanoate?

The InChIKey of methyl 3-amino-3-phenylpropanoate is XKIOBYHZFPTKCZ-UHFFFAOYSA-N.

What is the canonical SMILES of methyl 3-amino-3-phenylpropanoate?

The canonical SMILES of methyl 3-amino-3-phenylpropanoate is COC(=O)CC(C1=CC=CC=C1)N.

What is the CAS number of methyl 3-amino-3-phenylpropanoate?

The CAS number of methyl 3-amino-3-phenylpropanoate is 14898-52-3.