67654-57-3

Basic information

• Product Name: Methyl (R)-3-acetamido-3-phenylpropanoate
• Synonyms: (R)-methyl-3-acetamido-3-phenylpropanoate;METHYL (R)-3-ACETAMIDO-3-PHENYLPROPANOATE
• CAS NO: 67654-57-3
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.25
• Product Categories: API intermediates
• Mol File: 67654-57-3.mol

Chemical Properties

• Melting Point: 94-95 °C
• Boiling Point: 406.1 °C at 760 mmHg
• Flash Point: 199.4 °C
• Appearance: /
• Density: 1.114 g/cm³
• Vapor Pressure: 8.36E-07mmHg at 25°C
• Refractive Index: 1.513
• PKA: 14.78±0.46(Predicted)
• CAS DataBase Reference: Methyl (R)-3-acetamido-3-phenylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (R)-3-acetamido-3-phenylpropanoate(67654-57-3)
• EPA Substance Registry System: Methyl (R)-3-acetamido-3-phenylpropanoate(67654-57-3)

Safety Data

• Hazardous Substances Data: 67654-57-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (R)-3-acetamido-3-phenylpropanoate is used as a key intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its unique stereochemistry is crucial for the development of enantiomerically pure compounds, which are vital for ensuring the desired therapeutic effects and minimizing potential side effects of medications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Methyl (R)-3-acetamido-3-phenylpropanoate is utilized for the preparation of a wide range of biologically active molecules. Its involvement in the synthesis of these molecules contributes to the discovery and development of new pharmaceutical agents with improved efficacy and selectivity.
Used in Agrochemical Development:
Methyl (R)-3-acetamido-3-phenylpropanoate also plays a significant role in the agrochemical industry, where it is employed in the synthesis of enantiomerically pure compounds for use in pesticides and other agricultural chemicals. This ensures that the active ingredients are not only effective but also have minimal environmental impact.

InChI:InChI=1/C12H15NO3/c1-9(14)13-11(8-12(15)16-2)10-6-4-3-5-7-10/h3-7,11H,8H2,1-2H3,(H,13,14)/t11-/m1/s1

Upstream product

• 72569-96-1 methyl (Z)-3-acetylamino-3-phenylacrylate 
• 371-27-7 2,2,2-trifluoroethylbutyrate 
• 105900-59-2 methyl 3-acetamido-3-phenylpropanoate 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 67-56-1 methanol 
• 1426822-57-2 C₁₃H₁₄F₃NO₃ 
• 5661-55-2 4-phenylazetidin-2-one 
• 110425-60-0 N-acetyl-4-phenyl-β-propiolactam 
• 100-42-5 styrene 
• 98-86-2 acetophenone 
• 333380-82-8 N-((S)-1-phenylbut-3-enyl)acetamide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 75-36-5 acetyl chloride 

Downstream Products

• 136744-94-0 (R)-3-ethylamino-3-phenyl-1-propanol 
• 1236280-72-0 methyl (2S,3S)-3-(acetylamino)-2-fluoro-3-phenylpropanoate 
• 614-19-7 (R)-3-phenyl-3-aminopropionic acid 
• 170564-98-4 (R)-3-amino-3-phenyl-1-propanol 

Relevant articles and documents

Chiral ferrocene-indole diphosphine ligand as well as preparation method and application thereof

The invention relates to a chiral ferrocene-indole diphosphine ligand as well as a preparation method and application thereof. The specific preparation method comprises the following steps: dissolving an indole compound and a chiral ferrocene phosphine ac

Chiral ferrocene phosphine-indole aminophosphine ligand as well as preparation method and application thereof

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OPTICALLY ACTIVE BISPHOSPHINO METHANE AND PRODUCTION METHOD THEREFOR, AND TRANSITION METAL COMPLEX AND ASYMMETRIC CATALYST

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Nickel-catalyzed enantioselective umpolung hydrogenation for stereoselective synthesis of β-amido esters

Nickel complexes ligated by strongly donating diphosphines catalyze enantioselective hydrogenation for the preparation of acyclic and cyclic β-amido esters. A combination of acetic acid and indium powder provides protons and electrons to form nickel hydrido complexes under umpolung hydrogenation conditions.

2,3-BISPHOSPHINOPYRAZINE DERIVATIVE, METHOD FOR PRODUCING SAME, TRANSITION METAL COMPLEX, ASYMMETRIC CATALYST, AND METHOD FOR PRODUCING ORGANIC BORON COMPOUND

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P-Stereogenic N-Phosphine-Phosphite Ligands for the Rh-Catalyzed Hydrogenation of Olefins

We have identified a successful family of simple P-stereogenic N-phosphine-phosphite ligands for the Rh-catalyzed asymmetric hydrogenation of olefins. These catalysts show excellent enantiocontrol for α-dehydroamino acid derivatives and α-enamides (ee's u

Phosphite-thioether/selenoether Ligands from Carbohydrates: An Easily Accessible Ligand Library for the Asymmetric Hydrogenation of Functionalized and Unfunctionalized Olefins

A large family of phosphite-thioether/selenoether ligands has been easily prepared from accessible L-(+)-tartaric acid and D-(+)-mannitol and applied in the M-catalyzed (M=Ir, Rh) asymmetric hydrogenation of a broad number of substrates (46 in total). Its highly modular architecture has been crucial to maximize the catalytic performance. Improving most of the reported approaches, this ligand family presents a broad substrate scope. By selecting the ligand parameters high enantioselectivities (ee's up to 99 %) have therefore been achieved in a broad range of both, functionalized and unfunctionalized substrates. Interestingly, both enantiomers of the hydrogenation products can be usually achieved by changing the ligand parameters.

A Bulky Three-Hindered Quadrant Bisphosphine Ligand: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation of Functionalized Alkenes

A bulky three-hindered quadrant bisphosphine ligand, di-1-adamantylphosphino(tert-butylmethylphosphino)methane, named BulkyP*, has been synthesized via a convergent short pathway with chromatography-free procedures. The ligand is a crystalline solid and can be readily handled in air. Its rhodium(I) complex exhibits very high enantioselectivities and catalytic activities in the asymmetric hydrogenation of functionalized alkenes.

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

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Studies on N-activation for the lipase-catalyzed enantioselective preparation of β-amino esters from 4-phenylazetidin-2-one

The effect of N-substitution was examined for the enantio-selective lipase-catalyzed ring-opening reaction of racemic 4-phenylazetidin-2-one with methanol in dry organic solvents. Marked differences in the reactivity of various N-protected 4-phenylazetidin-2-ones were observed. Preparativescale reactions with Candida antarctica lipase B (Novozym 435 preparation) yielded N-acylated methyl (R)-3-amino-3- phenylpropanoates with enantiomeric excess (ee) values >99% in up to a 49% isolated yield, whereas Thermomyces lanuginosus lipase (Lipozyme TM IM) gave enantiomerically enriched methyl (S)-3-acetamido-3-phenylpropanoate. Candida antarctica lipase A catalyzed the cleavage of the N-chloroacetyl protective group, whereas all of the other examined lipases underwent the ring-opening reaction.