Methyl (3R)-3-acetamido-3-(4-methoxyphenyl)propanoate

Base Information

• Chemical Name: Methyl (3R)-3-acetamido-3-(4-methoxyphenyl)propanoate
• CAS No.: 810670-02-1
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.282
• DSSTox Substance ID: DTXSID80464449
• Mol file: 810670-02-1.mol

Synonyms:810670-02-1;Methyl (3R)-3-acetamido-3-(4-methoxyphenyl)propanoate;(R)-METHYL-3-ACETAMIDO-3-(4-METHOXY-PHENYL)-PROPANOATE;Benzenepropanoic acid, b-(acetylamino)-4-methoxy-, methylester, (bR)-;DTXSID80464449;AG-H-25806;Methyl(R)-3-acetamido-3-(4-methoxyphenyl)propanoate

Chemical Property of Methyl (3R)-3-acetamido-3-(4-methoxyphenyl)propanoate

Chemical Property:

• Vapor Pressure: 5.97E-08mmHg at 25°C
• Boiling Point: 440.3oC at 760 mmHg
• Flash Point: 220.1oC
• PSA: 64.63000
• Density: 1.129g/cm3
• LogP: 1.82640
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 251.11575802
• Heavy Atom Count: 18
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

METHYL-(R)-3-ACETAMIDO-3-(4-METHOXYPHENYL)PROPANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC(=O)OC)C1=CC=C(C=C1)OC
• Isomeric SMILES: CC(=O)N[C@H](CC(=O)OC)C1=CC=C(C=C1)OC

Technology Process of Methyl (3R)-3-acetamido-3-(4-methoxyphenyl)propanoate

There total 16 articles about Methyl (3R)-3-acetamido-3-(4-methoxyphenyl)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl β-(4-methoxyphenyl)-β-(acetylamino)acrylate → methyl (R)-3-acetylamino-3-(4-methoxyphenyl)propionate (434957-82-1,810670-02-1)

Guidance literature:

With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; (S)-1,1'-spirobiindan-7,7'-diyl 4-methoxyphenylphosphonite; In dichloromethane; at 20 ℃; for 36h; under 75006 Torr;

DOI:10.1021/jo049146x

Reference yield: 100.0%

hydrogen (1333-74-0) + (Z)-methyl 3-acetamido-3-(4-methoxyphenyl)-2-propenoate (434957-24-1) → methyl 3-acetamido-3-(4-methoxyphenyl)propanoate (100610-44-4,434957-82-1,810670-02-1)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; C₃₆H₂₉F₆NP₂; In methanol; at 20 ℃; for 24h; under 7600.51 Torr; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.200800418

Reference yield: 98.0%

(Z)-methyl 3-acetamido-3-(4-methoxyphenyl)-2-propenoate (434957-24-1) → methyl (R)-3-acetylamino-3-(4-methoxyphenyl)propionate (434957-82-1,810670-02-1)

Guidance literature:

With formic acid; nickel diacetate; triethylamine; (3S,3'S,4S,4'S,11bS,11'bS)-(+)-4,4'-di-t-butyl-4,4',5,5'-tetrahydro-3,3'-bi-3H-dinaphtho[2,1-c:1',2'-e]phosphepin; In 1,4-dioxane; at 60 ℃; for 24h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201407744

upstream raw materials:

acetic anhydride

hydrogen

(Z)-methyl 3-acetamido-3-(4-methoxyphenyl)-2-propenoate

methyl 3-acetamido-3-(4-methoxyphenyl)-2-propenoate

Refernces

• 1、 Li, Xiuxiu,You, Cai,Li, Shuailong,Lv, Hui,Zhang, Xumu. "Nickel-catalyzed enantioselective hydrogenation of β-(acylamino)acrylates: Synthesis of chiral β-amino acid derivatives". supporting information. p. 5130 - 5133. Retrieved 2017/11/06.
• 2、 Zhou, Xiao-Mao,Huang, Jia-Di,Luo, Li-Bin,Zhang, Cheng-Lu,Zheng, Zhuo,Hu, Xiang-Ping. "Readily available chiral phosphine-aminophosphine ligands derived from 1-phenylethylamine for Rh-catalyzed enantioselective hydrogenations". experimental part. p. 420 - 424. Retrieved 2010/07/02.