Methyl (3S)-3-acetamido-3-phenylpropanoate

Base Information

• Chemical Name: Methyl (3S)-3-acetamido-3-phenylpropanoate
• CAS No.: 67654-58-4
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.256
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20444043
• Nikkaji Number: J1.237.434H
• Wikidata: Q72486460
• Mol file: 67654-58-4.mol

Synonyms:67654-58-4;Methyl (3S)-3-acetamido-3-phenylpropanoate;Benzenepropanoic acid, b-(acetylamino)-, methyl ester, (bS)-;SCHEMBL1144523;DTXSID20444043;AKOS017342900;(S)-methyl 3-acetamido-3-phenylpropanoate;(S)-beta-(Acetylamino)benzenepropanoic acid methyl ester

Chemical Property of Methyl (3S)-3-acetamido-3-phenylpropanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 99-101 °C
• Refractive Index: 1.514
• Boiling Point: 406.066 °C at 760 mmHg
• PKA: 14.78±0.46(Predicted)
• Flash Point: 199.382 °C
• PSA: 52.32000
• Density: 1.115 g/cm³
• LogP: 1.94980
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 221.10519334
• Heavy Atom Count: 16
• Complexity: 247

Purity/Quality:

98%min ^*data from raw suppliers

(S)-Methyl2-acetamido-3-phenylpropanoate 97% ^*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=CC=C1
• Isomeric SMILES: CC(=O)N[C@@H](CC(=O)OC)C1=CC=CC=C1

Technology Process of Methyl (3S)-3-acetamido-3-phenylpropanoate

There total 25 articles about Methyl (3S)-3-acetamido-3-phenylpropanoate 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%

(E/Z)-methyl 3-acetamido-3-phenyl-2-propenoate → methyl (S)-3-acetylamino-3-phenylpropionate (67654-57-3,105900-59-2,67654-58-4)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; C₄₇H₄₃FeNOP₂; In toluene; for 12h; Inert atmosphere;

Reference yield: 90.0%

(3S)-methyl 3-amino-3-phenylpropanoate (37088-66-7) + acetyl chloride (75-36-5) → methyl (S)-3-acetylamino-3-phenylpropionate (67654-57-3,105900-59-2,67654-58-4)

Guidance literature:

With triethylamine; In chloroform; at 0 - 20 ℃; optical yield given as %ee;

DOI:10.1002/chem.200801582

Reference yield: 40.0%

methanol (67-56-1) + N-acetyl-4-phenyl-β-propiolactam (110425-60-0) → (S)-N-acetyl-4-phenylazetidin-2-one + (R)-N-acetyl-4-phenylazetidin-2-one + methyl (R)-3-acetamido-3-phenylpropanoate (67654-57-3) + methyl (S)-3-acetylamino-3-phenylpropionate (67654-57-3,105900-59-2,67654-58-4)

Guidance literature:

With lipase fromThermomyces lanuginosus immobilized on granulated silica; In tert-butyl methyl ether; at 23 ℃; for 48h; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/ejoc.201403467

upstream raw materials:

(E)-methyl 3-acetamido-3-phenyl-2-propenoate

N-((S)-1-phenylbut-3-enyl)acetamide

diazomethyl-trimethyl-silane

methyl (Z)-3-acetylamino-3-phenylacrylate

Refernces

• 1、 -. "Chiral ferrocene-indole diphosphine ligand as well as preparation method and application thereof". Paragraph 0067-0068. . Retrieved 2021/05/22.
• 2、 -. "2,3-BISPHOSPHINOPYRAZINE DERIVATIVE, METHOD FOR PRODUCING SAME, TRANSITION METAL COMPLEX, ASYMMETRIC CATALYST, AND METHOD FOR PRODUCING ORGANIC BORON COMPOUND". Paragraph 0262-0264. . Retrieved 2021/02/19.