DL-Homophenylalanine

Base Information

• Chemical Name: DL-Homophenylalanine
• CAS No.: 1012-05-1
• Deprecated CAS: 7636-28-4,109754-88-3
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 29224999
• UNII: NTL1IB8F3L
• DSSTox Substance ID: DTXSID80874100
• Nikkaji Number: J81.428H
• Wikidata: Q27285054
• ChEMBL ID: CHEMBL203873
• Mol file: 1012-05-1.mol

Synonyms:Butyric acid,2-amino-4-phenyl-, DL- (8CI);2-Amino-4-phenylbutanoic acid;2-Amino-4-phenylbutyricacid;DL-2-Amino-4-phenylbutyric acid;

Chemical Property of DL-Homophenylalanine

Chemical Property:

• Vapor Pressure: 9.3E-06mmHg at 25°C
• Melting Point: 282 °C (dec.)(lit.)
• Refractive Index: 1.569
• Boiling Point: 324.82 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 150.246 °C
• PSA: 63.32000
• Density: 1.164 g/cm³
• LogP: 1.73140
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Slightly), Aqueous Base (Slightly)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

98%,99%, ^*data from raw suppliers

DL-Homophenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(C(=O)O)N
• Uses: DL-Homophenylalanine (Lisinopril EP Impurity A) is an impurity of Lisinopril.

Technology Process of DL-Homophenylalanine

There total 39 articles about DL-Homophenylalanine 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: 96.0%

ethyl L-2-amino-4-phenylbutyrate (46460-23-5,46460-24-6,82830-84-0,124044-66-2) → D,L-homophenylalanine (1012-05-1)

Guidance literature:

With hydrogenchloride; In water; for 2.5h; Reflux;

DOI:10.1002/adsc.201600248

Reference yield: 82.0%

2-oxo-4-phenylbutyric acid (710-11-2) → D,L-homophenylalanine (1012-05-1)

Guidance literature:

With (S)-2-amino-(2-chlorophenyl)ethanoic acid; In water; acetonitrile; at 50 ℃; for 36h; Reflux; Inert atmosphere;

DOI:10.1021/acs.joc.0c01302

Reference yield: 74.3%

5-phenylethyl-imidazolidine-2,4-dione (120379-81-9) → D,L-homophenylalanine (1012-05-1)

Guidance literature:

With sodium hydroxide; In water; at 130 - 132 ℃; for 4h;

DOI:10.1016/j.tetasy.2004.02.026

upstream raw materials:

2-bromo-4-phenyl butanoic acid

(E)-2-oxo-4-phenyl-3-butenoic acid

2-oxo-4-phenylbutyric acid

bromo-phenethyl-malonic acid

Downstream raw materials:

2-(Naphthalene-1-sulfonylamino)-4-phenyl-butyric acid

2-benzoylamino-4-phenyl-butyric acid

2-Acetylsulfanyl-4-phenyl-butyric acid

(RS)-2-(acetylthio)-4-phenylbutanoyl-L-leucyl-L-phenylalanine N-methylamide

Refernces

• 1、 Regla, Ignacio,Luna, Hector,Perez, Herminia I.,Demare, Patricia,Bustos-Jaimes, Ismael,Zaldivar, Victor,Calcagno, Mario L.. "Enzymatic resolution of N-acetyl-homophenylalanine with mammalian kidney acetone powders". . p. 1285 - 1288. Retrieved 2004.
• 2、 Inada, Haruki,Furukawa, Keisuke,Shibuya, Masatoshi,Yamamoto, Yoshihiko. "One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols". . p. 15105 - 15108. Retrieved 2019.
• 3、 Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko. "Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine". . p. 11047 - 11059. Retrieved 2020/10/12.