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Methyl (R)-3-acetamido-3-phenylpropanoate is a chiral chemical compound with the molecular formula C12H15NO3. It is characterized by its non-superimposable mirror image and the (R)designation, which specifies its stereochemistry. Methyl (R)-3-acetamido-3-phenylpropanoate is widely recognized for its role in the pharmaceutical industry, particularly in the synthesis of drugs and active pharmaceutical ingredients (APIs). Its importance extends to the production of enantiomerically pure compounds, which are essential for the development of various pharmaceutical and agrochemical products. Methyl (R)-3-acetamido-3-phenylpropanoate is a key intermediate in the preparation of a diverse array of biologically active molecules, solidifying its value in medicinal chemistry.

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  • 67654-57-3 Structure
  • Basic information

    1. Product Name: Methyl (R)-3-acetamido-3-phenylpropanoate
    2. Synonyms: (R)-methyl-3-acetamido-3-phenylpropanoate;METHYL (R)-3-ACETAMIDO-3-PHENYLPROPANOATE
    3. CAS NO:67654-57-3
    4. Molecular Formula: C12H15NO3
    5. Molecular Weight: 221.25
    6. EINECS: N/A
    7. Product Categories: API intermediates
    8. Mol File: 67654-57-3.mol
  • Chemical Properties

    1. Melting Point: 94-95 °C
    2. Boiling Point: 406.1 °C at 760 mmHg
    3. Flash Point: 199.4 °C
    4. Appearance: /
    5. Density: 1.114 g/cm3
    6. Vapor Pressure: 8.36E-07mmHg at 25°C
    7. Refractive Index: 1.513
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 14.78±0.46(Predicted)
    11. CAS DataBase Reference: Methyl (R)-3-acetamido-3-phenylpropanoate(CAS DataBase Reference)
    12. NIST Chemistry Reference: Methyl (R)-3-acetamido-3-phenylpropanoate(67654-57-3)
    13. EPA Substance Registry System: Methyl (R)-3-acetamido-3-phenylpropanoate(67654-57-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 67654-57-3(Hazardous Substances Data)

67654-57-3 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.

Check Digit Verification of cas no

The CAS Registry Mumber 67654-57-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,7,6,5 and 4 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 67654-57:
(7*6)+(6*7)+(5*6)+(4*5)+(3*4)+(2*5)+(1*7)=163
163 % 10 = 3
So 67654-57-3 is a valid CAS Registry Number.
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

67654-57-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl (R)-3-acetamido-3-phenylpropanoate

1.2 Other means of identification

Product number -
Other names (R)-methyl-3-acetamido-3-phenylpropanoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:67654-57-3 SDS

67654-57-3Relevant articles and documents

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

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Paragraph 0071-0073, (2021/02/10)

PROBLEM TO BE SOLVED: To provide a novel optically active bisphosphine methane that is useful as a ligand for an asymmetric catalyst, has excellent oxidation resistance in the air, and is easy to handle, and to provide a transition metal complex using, as

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

Zhou, Jianrong Steve,Guo, Siyu,Zhao, Xiaohu,Chi, Yonggui Robin

supporting information, p. 11501 - 11504 (2021/11/16)

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

-

Paragraph 0262-0264, (2021/02/19)

Provided is a 2,3-bisphosphinopyrazine derivative represented by the following general formula (1), wherein R1, R2, R3, and R4 represent an optionally substituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, an optionally substituted cycloalkyl group, an optionally substituted adamantyl group, or an optionally substituted phenyl group, R5 represents an optionally substituted alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group, each R5 may be the same group or a different group, R6 represents a monovalent substituent, n denotes an integer of 0 to

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

-

Paragraph 0067-0068, (2021/05/22)

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

-

Paragraph 0046-0047, (2021/05/22)

The invention discloses a chiral ferrocene phosphine-indole aminophosphine ligand as well as a preparation method and application thereof. The preparation method comprises the following steps: dissolving a chiral ferrocene phosphine-indole intermediate in

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

Biosca, Maria,De La Cruz-Sánchez, Pol,Diéguez, Montserrat,Pàmies, Oscar

, p. 4730 - 4739 (2020/05/08)

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

Margalef, Jèssica,Borràs, Carlota,Alegre, Sabina,Alberico, Elisabetta,Pàmies, Oscar,Diéguez, Montserrat

, p. 2142 - 2168 (2019/04/13)

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

Sawatsugawa, Yuuki,Tamura, Ken,Sano, Natsuhiro,Imamoto, Tsuneo

supporting information, p. 8874 - 8878 (2019/11/03)

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

Li, Xiuxiu,You, Cai,Li, Shuailong,Lv, Hui,Zhang, Xumu

supporting information, p. 5130 - 5133 (2017/11/06)

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.

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

Sundell, Riku,Kanerva, Liisa T.

, p. 1500 - 1506 (2015/03/04)

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.

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