Methyl (R)-aminophenylacetate

Base Information

• Chemical Name: Methyl (R)-aminophenylacetate
• CAS No.: 24461-61-8
• Molecular Formula: C9H11 N O2
• Molecular Weight: 165.192
• Hs Code.: 2922499990
• European Community (EC) Number: 246-273-1
• UNII: 858LQZ6H2K
• DSSTox Substance ID: DTXSID90947339
• Nikkaji Number: J62.815H
• Wikidata: Q27269613
• ChEMBL ID: CHEMBL502179
• Mol file: 24461-61-8.mol

Synonyms:24461-61-8;Methyl (R)-aminophenylacetate;methyl (2R)-2-amino-2-phenylacetate;(R)-Methyl 2-amino-2-phenylacetate;Methyl phenylglycinate, D-;UNII-858LQZ6H2K;858LQZ6H2K;EINECS 246-273-1;EC 246-273-1;(R)-phenylglycine methylester;D-Phenylglycine methyl;D-methyl phenylglycinate;(R)-PGME;SCHEMBL318862;METHYL D-PHENYLGLYCINATE;CHEMBL502179;DTXSID90947339;METHYL (R)-2-PHENYLGLYCINATE;AKOS010395581;METHYL PHENYLGLYCINATE, (-)-;AC-5678;METHYL (R)-(-)-2-PHENYLGLYCINATE;CS-0356354;D-.ALPHA.-PHENYLGLYCINE METHYL ESTER;METHYL (R)-2-AMINO-2-PHENYLACETATE;EN300-344225;Q27269613;Benzeneacetic acid, .alpha.-amino-, methyl ester, (R)-;BENZENEACETIC ACID, .ALPHA.-AMINO-, METHYL ESTER, (.ALPHA.R)-

Chemical Property of Methyl (R)-aminophenylacetate

Chemical Property:

• Boiling Point: 238.9±20.0 °C(Predicted)
• PKA: 6.70±0.10(Predicted)
• PSA: 52.32000
• Density: 1.126±0.06 g/cm3(Predicted)
• LogP: 1.55970
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 153

Purity/Quality:

99.9% ^*data from raw suppliers

METHYL-(2R)-2-AMINO-2-PHENYLACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl (R)-aminophenylacetate

There total 107 articles about Methyl (R)-aminophenylacetate 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: 98.0%

methanol (67-56-1) + (S)-2-phenylglycine (2935-35-5) → (S)-Phenylglycine methyl ester (6591-61-3,24461-61-8,26682-99-5,37760-98-8)

Guidance literature:

With thionyl chloride; at 0 ℃; for 2h;

DOI:10.1016/j.bmcl.2009.05.048

Reference yield: 92.0%

(S)-methyl 2-(benzyloxycarbonylamino)-2-phenylacetate (147780-61-8) → (S)-Phenylglycine methyl ester (6591-61-3,24461-61-8,26682-99-5,37760-98-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃;

DOI:10.1002/adsc.201100615

Reference yield: 92.0%

L-2-phenylglycine methyl ester hydrochloride (15028-39-4,13226-98-7) → (S)-Phenylglycine methyl ester (6591-61-3,24461-61-8,26682-99-5,37760-98-8)

Guidance literature:

With ammonia; In diethyl ether; for 4h;

DOI:10.1002/cbic.201600550

upstream raw materials:

methanol

phenylglycin

2-(benzyloxycarbonylamino)-2-phenylacetic acid

phenylacetonitrile

Downstream raw materials:

L-phenylglycine amide

(4-chloro-benzoylamino)-phenyl-acetic acid but-2t-enyl ester

(4-chloro-benzoylamino)-phenyl-acetic acid (Z)-3-methyl-pent-2-en-4-ynyl ester

(4-Chloro-benzoylamino)-phenyl-acetic acid (E)-penta-2,4-dienyl ester

Refernces

• 1、 Faigl, Ferenc,Matravoelgyi, Bela,Holczbauer, Tamas,Czugler, Matyas,Madarasz, Janos. "Resolution of 1-[2-carboxy-6-(trifluoromethyl)phenyl]-1H-pyrrole-2- carboxylic acid with methyl (R)-2-phenylglycinate, reciprocal resolution and second order asymmetric transformation". . p. 1879 - 1884. Retrieved 2011.
• 2、 Basso, Alessandra,Braiuca, Paolo,De Martin, Luigi,Ebert, Cynthia,Gardossi, Lucia,Linda, Paolo. "D-Phenylglycine and D-4-hydroxyphenylglycine methyl esters via penicillin G acylase catalysed resolution in organic solvents". . p. 1789 - 1796. Retrieved 2000.
• 3、 Chang, Sukbok,Gwon, Yunyeong,Kim, Dongwook,Lee, Minhan. "Iridium-Catalyzed Amidation of in Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters". . p. 1088 - 1093. Retrieved 2022/02/10.
• 4、 Jiang, Hong,Yang, Kuiwei,Zhao, Xiangxiang,Zhang, Wenqiang,Liu, Yan,Jiang, Jianwen,Cui, Yong. "Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography". supporting information. p. 390 - 398. Retrieved 2021/01/13.