Methyl N-acetyl-DL-phenylalaninate

Base Information

• Chemical Name: Methyl N-acetyl-DL-phenylalaninate
• CAS No.: 21156-62-7
• Molecular Formula: C12H15NO3
• Molecular Weight: 221.256
• Hs Code.: 2924299090
• NSC Number: 43116
• UNII: Q85F0D40UT
• DSSTox Substance ID: DTXSID00874324
• Nikkaji Number: J31.471D
• Wikidata: Q27287108
• ChEMBL ID: CHEMBL445907
• Mol file: 21156-62-7.mol

Synonyms:Methyl 2-(acetylamino)-3-phenylpropanoate;Methyl N-acetyl-DL-phenylalaninate;methyl 2-acetamido-3-phenylpropanoate;N-acetyl-DL-phenylalanine methyl ester;Q85F0D40UT;62436-70-8;DL-N-Acetylphenylalanine methyl ester;Methyl (+/-)-N-acetylphenylalaninate;Rac-N-acetylphenylalanine methyl ester;Phenylalanine, N-acetyl-, methyl ester;UNII-Q85F0D40UT;Methyl N-acetyl-L-phenylalaninate, (+/-)-;N-acetyl-d,l-phenylalanine methyl ester;2-Acetylamino-3-phenyl-propionic acid methyl ester;Acetyl-L-phenylalanine methyl ester;N-Acetyl-L-phenylalanine methyl ester;N-Acetylphenylalanine methyl ester;NSC-43116;(S)-N-Acetyl-3-phenylalanine methyl ester;Maybridge3_005305;SCHEMBL803579;CHEMBL445907;DTXSID00874324;IKGHIFGXPVLPFD-UHFFFAOYSA-N;HMS1446B03;NSC43116;AKOS008935247;CCG-245375;IDI1_016692;methyl 2-acetylamino-3-phenylpropionate;PHENYLALANINE-N-ACETYL,METHYL ESTER;FT-0634934;FT-0638101;AB-131/40897220;Q27287108;1-Benzyl-3-trifluoromethyl-pyrrolidine-3-carboxylicacid

Chemical Property of Methyl N-acetyl-DL-phenylalaninate

Chemical Property:

• Vapor Pressure: 2.55E-06mmHg at 25°C
• Melting Point: 88 °C
• Refractive Index: 1.514
• Boiling Point: 391 °C at 760 mmHg
• PKA: 14.74±0.46(Predicted)
• Flash Point: 190.3 °C
• PSA: 55.40000
• Density: 1.117 g/cm³
• LogP: 1.29770
• Storage Temp.: 2-8°C
• 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

Acetyl-D-phenylalanine methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC=CC=C1)C(=O)OC

Technology Process of Methyl N-acetyl-DL-phenylalaninate

There total 105 articles about Methyl N-acetyl-DL-phenylalaninate 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 (Z)-2-(acetylamino)-3-phenylpropenoate (60676-51-9) → (R)-N-acetylphenylalanine methyl ester (21156-62-7)

Guidance literature:

With hydrogen; [((1R,2S)-DPAMPP)Rh(COD)]BF₄; In methanol; at 20 ℃; for 1h; under 38000 Torr;

DOI:10.1016/S0040-4020(00)00481-6

Reference yield: 100.0%

N-acetyl dehydrophenylalanine methyl ester (52386-78-4) → N-acetylphenylalanine methyl ester (21156-62-7,3618-96-0,62436-70-8)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; C₄₂H₃₆NO₂P; hydrogen; In dichloromethane; at 20 ℃; for 24h; under 760.051 Torr; Inert atmosphere; Glovebox; Schlenk technique;

Reference yield: 100.0%

N-acetyl dehydrophenylalanine methyl ester (52386-78-4) → (R)-N-acetylphenylalanine methyl ester (21156-62-7)

Guidance literature:

With {(1,5-cyclooctadiene)Rh(1,2-bis((2R,5R)-2,5-diethylphospholano)benzene)}triflate; hydrogen; In methanol; at 20 - 25 ℃; under 1551.4 Torr;

upstream raw materials:

(R,S)-N-acetyl phenylalanine

diazomethane

methanol

4-benzylidene-2-methyl-2-oxazolin-5-one

Downstream raw materials:

(R)-N-acetylphenylalanin

(S)-2-acetylamino-3-phenylpropanoic acid

(S)-N-acetylphenylalanine

C₁₂H₁₄N₂O₄

Refernces

• 1、 Alame, Mohamad,Pestre, Nathalie,De Bellefona, Claude. "Extensive re-investigations of pressure effects in rhodium-catalyzed asymmetric hydrogenations". . p. 898 - 908. Retrieved 2008.
• 2、 Tsuruta, Hideyuki,Imamoto, Tsuneo,Yamaguchi, Kentaro,Gridnev, Ilya D.. "Evidence for the importance of conformational equilibria in Rh-diphosphine complexes for the enantioselection in Rh-catalyzed asymmetric hydrogenation". . p. 2879 - 2882. Retrieved 2005.
• 3、 Aloui, A.,De Bellefon, C.,Delbecq, F.,Sautet, P.. "Further insight in the minor/major concept using hydrogen pressure effect in asymmetric hydrogenation". . p. 214 - 222,9. Retrieved 2012.
• 4、 Milligan, John A.,Busacca, Carl A.,Senanayake, Chris H.,Wipf, Peter. "Hydrophosphination of Bicyclo[1.1.0]butane-1-carbonitriles". . p. 4300 - 4303. Retrieved 2016.
• 5、 Sokolovskaya, Marina V.,Lyubimov, Sergey E.,Mikhel, Igor S.,Birin, Kirill P.,Davankov, Vadim A.. "Synthesis of a new bulky phosphite ligand and its application in the enantioselective hydrogenation". . p. 230 - 233. Retrieved 2018.
• 6、 Tommasino,Casalta, Magali,Breuzard, Jeremy A.J,Lemaire, Marc. "Asymmetric hydrogenation of enamides with catalysts containing chiral thiourea ligands". . p. 4835 - 4841. Retrieved 2000.
• 7、 Auras, Stefanie,Trapp, Oliver. "Scorpio-Ligand: Synthesis of Biphenyl-Dihydroazepine Phosphoramidite Ligands for Asymmetric Hydrogenation". . . Retrieved 2021.
• 8、 Glaser,Geresh. "". . p. 2527. Retrieved 1977.
• 9、 Robert, Fabien,Sinou, Denis. "Rhodium-catalyzed reduction of α-amino acid precursors using chiral 4-(diphenylphosphanyl)-1-(dialkylamino)butane ligands". . p. 99 - 102. Retrieved 2000.
• 10、 Achiwa. "-". . p. 8265. Retrieved 1976.