(R)-2-Amino-3-phenylpropionic acid methylester

Base Information

• Chemical Name: (R)-2-Amino-3-phenylpropionic acid methylester
• CAS No.: 21685-51-8
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID501306319
• Nikkaji Number: J31.466H
• ChEMBL ID: CHEMBL53697
• Mol file: 21685-51-8.mol

Synonyms:Alanine,phenyl-, methyl ester, D- (8CI); (+)-Phenylalanine methyl ester;(R)-2-Amino-3-phenylpropionic acid methyl ester; (R)-Phenylalanine methylester; Methyl D-phenylalaninate; NSC 522409; O-Methyl-D-phenylalanine

Chemical Property of (R)-2-Amino-3-phenylpropionic acid methylester

Chemical Property:

• Boiling Point: 264.2°Cat760mmHg
• PKA: 7.13±0.33(Predicted)
• Flash Point: 126°C
• PSA: 52.32000
• Density: 1.1g/cm³
• LogP: 1.42970
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)N
• Isomeric SMILES: COC(=O)[C@@H](CC1=CC=CC=C1)N

Technology Process of (R)-2-Amino-3-phenylpropionic acid methylester

There total 45 articles about (R)-2-Amino-3-phenylpropionic acid methylester 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%

methanol (67-56-1) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → D-phenylalanine methyl ester (21685-51-8)

Guidance literature:

methanol; With acetyl chloride; at 0 ℃; for 0.5h;

D-(R)-phenylalanine; for 3h; Reflux;

DOI:10.1016/j.bmcl.2010.02.033

Reference yield: 85.0%

methyl 2-amino-3-phenylpropanoate hydrochloride (5619-07-8) → L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) + D-phenylalanine methyl ester (21685-51-8)

Guidance literature:

at 30 ℃; for 0.333333h; Yields of byproduct given; enzyme alcalase from Bacillus licheniforms; pH 8.0;

DOI:10.1039/c39860001514

Reference yield: 73.0%

(2R,5S)-2-Benzyl-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine (87900-19-4) → L-Valine methyl ester (4070-48-8) + methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + D-phenylalanine methyl ester (21685-51-8)

Guidance literature:

With hydrogenchloride; for 10h; Ambient temperature;

upstream raw materials:

DL-phenylalanine methyl ester

(2R,5S)-2-Benzyl-5-tert-butyl-3,6-dimethoxy-2,5-dihydro-pyrazine

(2R,5S)-2-Benzyl-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine

methyl 2-amino-3-phenylpropanoate hydrochloride

Downstream raw materials:

Z-L-Leu-D-Phe-OMe

Boc-L-Leu-D-Phe-OMe

N-Benzyloxycarbonyl-β-O-benzyl-Asp-D-Phe-methylester

methyl (tert-butoxycarbonyl)-L-phenylalanyl-L-phenylalaninate

Refernces

• 1、 Zhu, Chengfeng,Tang, Haitong,Yang, Keke,Fang, Yu,Wang, Kun-Yu,Xiao, Zhifeng,Wu, Xiang,Li, Yougui,Powell, Joshua A.,Zhou, Hong-Cai. "Homochiral Dodecanuclear Lanthanide "cage in Cage" for Enantioselective Separation". supporting information. p. 12560 - 12566. Retrieved 2021/08/23.
• 2、 Debia, Natalí P.,Rodríguez, Juan J.P.,da Silveira, Carolina H.,Chaves, Otavio A.,Iglesias, Bernardo A.,Rodembusch, Fabiano S.,Lüdtke, Diogo S.. "Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution". . . Retrieved 2020/04/27.