DL-Homophenylalanine

White to off-white powder

To a stirred solution of horao-phenyS alanine (3.5 g, 19.5 mraol) In 60 mL MeOH was added concentrated H2SO4 via syringe (1.03 ml, , 19, 5 mmol), the reaction mixture was stirred at rt for 5 minutes and heated up to 70 C for 120 minutes. The reaction mixture was cooled down to rt, MeOH was evaporated and the mixture was diluted with 100 mL EtOAc, washed with NaHCOj, water, brine, then dried over Na2S0.4. The solvent was then removed to give the title compound as a tight yellow solid ( 3.63g, 96, 3%). The material was used without further purification. MS (ES+): m/z =194(M+1) 1H NMR (400 MHz, CHLOROFORM-D) S - 1.79; 1, 89 (m, 1 H) 2.01; 2.10 (m, 1 H) 2.67; 2.77 (m, 2 H) 3.43 (dd, .7=7.83, 5.31 Hz, 1 H) 3, 68 (s, 3 H) 7.15; 7.21 (m, 3 H) 7, 26; 7.29 (m, 2 H)D, L-2-Amino-4-phenyl-butyric acid (248 mg, 1.38 mmol) was suspended in MeOH (5 mL), cone. H2SO4 (0.1 mL) was added, and the mixture heated to reflux. After 48 hours the reaction was cooled to room temperature, and basified with 4 M NaOH. The product was extracted with EtOAc (50 mL), and the organic layer washed with brine. 4 Nu HCl in dioxane solution (0.5 mL) was added, followed by ethyl ether (20 mL) and hexane (20 mL). D, L-2- Amino-4-phenyl-butyric acid methyl ester precipitated as white needles and was collected by filtration and dried to give 130 mg (crop 1). MS(ES) m/z 193.5 (MH+); MS calc: 193.25 (M)

DL-Homophenylalanine (Lisinopril EP Impurity A) is an impurity of Lisinopril.

Molecular Weight:179.22
XLogP3:-1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:179.094628657
Monoisotopic Mass:179.094628657
Topological Polar Surface Area:63.3
Heavy Atom Count:13
Complexity:164
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes