DL-beta-(3-Bromophenyl)alanine

A mixture of 200 grams (1.08 mol) of 3-bromobenzaldehyde, 112 grams (1.08 mol) of malonic acid, and 166.5 g (2.16 mol) of ammonium acetate was suspended in 1.125 liters of absolute ethanol. The mixture was mechanically stirred and brought to reflux temperature, whereupon the solution clarified. The mixture was kept at reflux for 16 h, and a precipitate formed. The mixture was chilled to 0° C., and the solid product was collected by filtration and washed with cold ethanol to yield 184 grams (70percent) of 3-amino-3-(3-bromophenyl)propanoic acid as a white solid which was carried forward without further purification or analytical characterization.A solution of 3-bromobenzaldehyde (50 mL, 0.43 mol), malonic acid (49.09 g, 0.47 mol) and ammonium acetate (49.73 g, 0.65 mol) in absolute ethanol (300 mL) was refluxed overnight then cooled to room temperature. To a mixture of 2-1 (50 g, 0.21 mol) in absolute ethanol (400 mL), concentrated sulfuric acid (12.8 mL) was added slowly. The mixture was refluxed overnight, then cooled to room temperature and carefully quenched with saturated aqueous sodium bicarbonate. The mixture was diluted with water then extracted with ethyl acetate. The organic layer was extracted twice with aqueous HCl (2N). The aqueous layer was basified with aqueous NaOH (2N) and extracted three times with ethyl acetate. These three organic layers were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give ethyl 3-amino-3-(3-bromophenyl)propanoate; (2-2, 25 g).Thionylchloride (1 equiv) was added dropwise to the solution of anhydrous methanol at a rate to maintain the temperature below 5 C. After 30 min, beta phenylalanine 9a-9l (3 equiv) was added in the reaction mixture at 65 C for 6 h, respectively. Then the anhydrous methanol was removed under reduced pressure, final white solid was obtained.

Molecular Weight:244.08
XLogP3:-1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:242.98949
Monoisotopic Mass:242.98949
Topological Polar Surface Area:63.3
Heavy Atom Count:13
Complexity:187
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes