810670-03-2

Basic information

• Product Name: Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate
• Synonyms: (R)-methyl-3-acetamido-3-(4-chlorophenyl)propanoate;METHYL (R)-3-ACETAMIDO-3-(4-CHLOROPHENYL)PROPANOATE
• CAS NO: 810670-03-2
• Molecular Formula: C12H14ClNO3
• Molecular Weight: 255.7
• Mol File: 810670-03-2.mol

Chemical Properties

• Boiling Point: 435.6oC at 760 mmHg
• Flash Point: 217.3oC
• Appearance: /
• Density: 1.215g/cm3
• Vapor Pressure: 8.63E-08mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate(810670-03-2)
• EPA Substance Registry System: Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate(810670-03-2)

Safety Data

• Hazardous Substances Data: 810670-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a building block for the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Organic Chemistry as a Reagent:
In the field of organic chemistry, Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate serves as a valuable reagent. It can be employed in a range of chemical reactions to facilitate the formation of desired products, contributing to the advancement of chemical research and the discovery of novel compounds.
Used in the Production of Biologically Active Compounds:
Due to its structural features and reactivity, Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate is used in the production of biologically active compounds. These compounds can have potential applications in medicine, such as in the treatment of various diseases or conditions, by interacting with specific biological targets.
Used in Research and Development:
Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate is also used in research and development settings. Scientists and researchers leverage its properties to explore new chemical reactions, investigate its interactions with other molecules, and understand its role in biological systems, which can lead to the discovery of new therapeutic agents or applications.

InChI:InChI=1/C12H14ClNO3/c1-8(15)14-11(7-12(16)17-2)9-3-5-10(13)6-4-9/h3-6,11H,7H2,1-2H3,(H,14,15)/t11-/m1/s1

Upstream product

• 99-91-2 para-chloroacetophenone 
• 22027-53-8 methyl 3-(4-chlorophenyl)-3-oxopropanoate 
• 90956-85-7 ethyl 3-amino-3-(4-chlorophenyl)acrylate 
• 104-88-1 4-chlorobenzaldehyde 
• 67-56-1 methanol 
• 1426822-63-0 C₁₃H₁₃ClF₃NO₃ 
• 19947-39-8 3-amino-3-(4-chlorophenyl)propionic acid 
• 434957-10-5 methyl (Z)-3-acetylamino-3-(p-chlorophenyl)acrylate 
• 108-24-7 acetic anhydride 
• 552838-53-6 methyl 3-acetamido-3-(4-chlorophenyl)-2-propenoate 

Relevant articles and documents

Nickel-catalyzed enantioselective hydrogenation of β-(acylamino)acrylates: Synthesis of chiral β-amino acid derivatives

The nickel-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates has been developed, affording chiral β-amino acid derivatives with excellent yields (95-99% yield) and enantioselectivities (97-99% ee). With the Ni-Binapine system, high enantioselectivities (98-99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of β-alkyl and β-aryl β-(acylamino)acrylates. The synthesis of chiral β-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.

Carica papaya lipase catalysed resolution of β-amino esters for the highly enantioselective synthesis of (S)-dapoxetine

An efficient synthesis of the (S)-3-amino-3-phenylpropanoic acid enantiomer has been achieved by Carica papaya lipase (CPL) catalysed enantioselective alcoholysis of the corresponding racemic N-protected 2,2,2-trifluoroethyl esters in an organic solvent. A high enantioselectivity (E > 200) was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. Based on the resolution of a series of amino acids, it was found that the structure of the substrate has a profound effect on the CPL-catalysed resolution. The enantioselectivity and reaction rate were significantly enhanced by switching the conventional methyl ester to an activated trifluoroethyl ester. When considering steric effects, the substituted phenyl and amino groups should not both be large for the CPL-catalysed resolution. The mechanism of the CPL-catalysed enantioselective alcoholoysis of the amino acids is discussed to delineate the substrate requirements for CPL-catalysed resolution. Finally, the reaction was scaled up, and the products were separated and obtained in good yields (≥ 80 %). The (S)-3-amino-3- phenylpropanoic acid obtained was used as a key chiral intermediate in the synthesis of (S)-dapoxetine with very high enantiomeric excess (> 99 %). A carica papaya lipase catalysed resolution of N-protected β-phenylalanine esters has been developed. High enantioselectivity was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. After 50 % conversion, the products were separated and used as key chiral intermediates for the synthesis of (S)-dapoxetine with > 99 % ee. Copyright

Highly efficient iridium-catalyzed asymmetric hydrogenation of unprotected β-enamine esters

A highly efficient and enantioselective hydrogenation of unprotected β-enamine esters catalyzed by Ir-(S,S)-f-Binaphane complex has been developed. This methodology provides straightforward access to free β-amino acids in high yields with excellent enantioselectivities up to 97% ee and high reactivities (TON > 5000).

Readily available chiral phosphine-aminophosphine ligands derived from 1-phenylethylamine for Rh-catalyzed enantioselective hydrogenations

A series of new chiral phosphine-aminophosphine ligands have been prepared via a two- or three-step transformation from commercially available and inexpensive (S)-1-phenylethylamine, and successfully used in the rhodium-catalyzed asymmetric hydrogenation

Chiral 1-phenylethylamine-derived phosphine-phosphoramidite ligands for highly enantioselective Rh-catalyzed hydrogenation of β-(acylamino) acrylates: Significant effect of substituents on 3,3′-positions of binaphthyl moiety

A series of new chiral phosphine-phosphoramidite ligands with a 3,3′-substituted binaphthyl moiety were prepared from 1-phenylethylamine, and successfully applied in the Rh-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates. The research disclosed that the substituents on the 3,3′-positions of binaphthyl moiety significantly influenced the enantioselectivity.

Practical P-chiral phosphane ligand for Rh-catalyzed asymmetric hydrogenation

A highly electron-donating and conformationally rigid P-chiral bis(trialkylphospholane) ligand 2 (DuanPhos) has been prepared in both enantiomeric forms through a concise synthesis. Rh-2 complex has exhibited remarkably high enantio-selectivities (up to >99% ee) and reactivities (up to 10,000 TON) for the hydrogenation of a wide variety of functionalized prochiral alkenes (5 different types), which provides a very practical catalytic system for the preparation of various synthetically useful chiral compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Practical Rh(I)-catalyzed asymmetric hydrogenation of β-(acylamino) acrylates using a new unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligand: Crucial influence of an N-H proton in the ligand

(Chemical Equation Presented) Excellent enantioselectivities and high turnovers (S/C = 5000) were achieved in the Rh(I)-catalyzed asymmetric hydrogenation of both β-aryl-and β-alkyl-β-(acylamino)acrylates with a new unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligand, and the presence of an N-H proton in the ligand was demonstrated to have a crucial role in the enantioselectivity.

Rhodium-catalyzed asymmetric hydrogenation of functionalized olefins using monodentate spiro phosphoramidite ligands

Novel chiral monodentate phosphorus ligands, SIPHOS, were conveniently synthesized from 1,1′-spirobiindane-7,7′-diol. The Rh complexes of SIPHOS can catalyze the hydrogenation of α-dehydroamino esters in mild conditions, providing α-amino acid derivatives

Synthesis of monodentate chiral spiro phosphonites and the electronic effect of ligand in asymmetric hydrogenation

New monodentate chiral phosphonites were synthesized from enantiomerically pure 1,1′-spirobiindane-7,7′-diol. The phosphonites 2 were efficient ligands for the Rh-catalyzed asymmetric hydrogenation of α- and β-dehydroamino acid derivatives, providing the

A bisphosphepine ligand with stereogenic phosphorus centers for the practical synthesis of β-aryl-β-amino acids by asymmetric hydrogenation

Excellent enantioselectivities and reactivities were observed in the hydrogenation of a variety of methyl (Z)-β-aryl-β-(acetyl-amino)acrylates in the presence of a rhodium catalyst with the chiral ligand binapine (see scheme). This bisbinaphthophosphepine