(2S)-2-amino-2-phenylpropanoic acid

Base Information

• Chemical Name: (2S)-2-amino-2-phenylpropanoic acid
• CAS No.: 13398-26-0
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID901335235
• Nikkaji Number: J35.826F
• ChEMBL ID: CHEMBL3085306
• Mol file: 13398-26-0.mol

Synonyms:13398-26-0;(2S)-2-amino-2-phenylpropanoic acid;(S)-2-amino-2-phenylpropanoic acid;2-phenyl-d-alanine;(S)-2-AMINO-2-PHENYL-PROPIONIC ACID;(2S)-2-AMINO-2-PHENYLPROPANOICACID;2-(s)-phenylalanine;Benzeneacetic acid, a-amino-a-methyl-, (aS)-;SCHEMBL222049;CHEMBL3085306;HTCSFFGLRQDZDE-VIFPVBQESA-N;DTXSID901335235;(S)-2-amino-2-phenylpropanoicacid;(S)-2-Amino-2-phenylpropionic acid;MFCD07371947;(R)-ALPHA-METHYL-PHENYLGLYCINE;AKOS006287023;AB33354;(+)-(2S)-2-amino-2-phenylpropionic acid;EN300-127462

Chemical Property of (2S)-2-amino-2-phenylpropanoic acid

Chemical Property:

• Melting Point: 294 °C
• Boiling Point: 298.5 °C at 760 mmHg
• PKA: 1.99±0.10(Predicted)
• Flash Point: 134.3 °C
• PSA: 63.32000
• Density: 1.197 g/cm³
• LogP: 1.64540
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 175

Purity/Quality:

99%, ^*data from raw suppliers

(S)-alpha-methylphenylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2S)-2-amino-2-phenylpropanoic acid

There total 26 articles about (2S)-2-amino-2-phenylpropanoic acid 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%

(R)-1-phenyl-ethyl-amine (3886-69-9) + 5-methyl-5-phenylimidazolidin-2,4-dione (6843-49-8,27539-12-4,99571-24-1,101693-73-6) → (S)-2-methyl-2-phenylglycine (13398-26-0,6945-32-0)

Guidance literature:

(R)-1-phenyl-ethyl-amine; 5-methyl-5-phenylimidazolidin-2,4-dione; With sodium hydroxide; In methanol; water; at 55 ℃; for 0.5h;

With water; at 160 ℃; for 4h;

With hydrogenchloride; In water; at 25 ℃; Product distribution / selectivity;

Reference yield: 97.0%

5-methyl-5-phenylimidazolidin-2,4-dione (6843-49-8,27539-12-4,99571-24-1,101693-73-6) → (S)-2-methyl-2-phenylglycine (13398-26-0,6945-32-0)

Guidance literature:

5-methyl-5-phenylimidazolidin-2,4-dione; With sodium hydroxide; (R)-1-phenyl-ethyl-amine; In ethanol; water; at 50 ℃; for 1.5h;

With water; at 140 ℃; for 4h;

With hydrogenchloride; In water; at 25 ℃; Product distribution / selectivity;

Reference yield: 90.8%

(S)-2-Benzoylamino-2-phenyl-propionic acid methyl ester (169566-73-8) → (S)-2-methyl-2-phenylglycine (13398-26-0,6945-32-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 12h;

DOI:10.1002/hlca.19950780305

upstream raw materials:

DL-α-methylphenylglycine amide

methyl (S)-2-amino-2-phenylpropanoate

(6S)-6-tert-Butyl-3,6-dihydro-5-methoxy-3-methyl-3-phenyl-2H-1,4-oxazin-2-on

(S)-2-Benzoylamino-2-phenyl-propionic acid methyl ester

Downstream raw materials:

(S)-N²-<(benzyloxy)carbonyl>-2-methyl-2-phenylglycine

(S)-2-phenyl-2-(toluene-4-sulfonylamino)-propionic acid

N-(tert-butoxycarbonyl)-2-phenyl-D-alanine

(1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamine hydrochloride

Refernces

• 1、 Leonard, Daniel J.,Ward, John W.,Clayden, Jonathan. "Asymmetric α-arylation of amino acids". . p. 105 - 109. Retrieved 2018/10/15.
• 2、 -. "UNNATURAL AMINO ACIDS". Paragraph 00190; 00296. . Retrieved 2018/07/05.