3-AMINO-3-(4-CHLOROPHENYL)PROPIONIC ACID

off-white powder

To 25 mL of ethanol were added 5.00 g (35.6 mmol) of 4-chlorobenzaldehyde, 3.70 g (35.6 mmol) of malonic acid and 4.10 g (53.2 mmol) of ammonium acetate, and the mixture was reacted while stirring under reflux (75 to 80°C) for 8 hours. After completion of the reaction, the obtained reaction mixture was stirred at room temperature for 1 hour and then filtered to give 5.9 g of 3-amino-3-(4-chlorophenyl)propionic acid (racemic mixtures) (isolation yield based on 4-chlorobenzaldehyde: 82.3percent) as white powder. Incidentally, physical properties of the 3-amino-3-(4-chlorophenyl)propionic acid (racemic mixtures) were as follows. General procedure: A mixture of appropriate aldehyde 2.40 g (1-15), 2.44 g ofmalonic acid and 3.54 g of ammonium acetate (1:1.1:2.3), in 200mLof the 1-butanol was refluxed for 1.5-2 h until the evolution of CO2ceased. The precipitate formed was filtered and washed withboiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and100mL of water. Precipitates were dried at 80-100 °C for 8-10 h.Purity of product was checked by TLC, and yield obtained about65-80percent in each reaction.To 25 mL of ethanol were added 5.00 g (35.6 mmol) of 4-chlorobenzaldehyde, 3.70 g (35.6 mmol) of malonic acid and 4.10 g (53.2 mmol) of ammonium acetate, and the mixture was reacted while stirring under reflux (75 to 80°C) for 8 hours. After completion of the reaction, the obtained reaction mixture was stirred at room temperature for 1 hour and then filtered to give 5.9 g of General procedure: A mixture of appropriate aldehyde 2.40 g (1-15), 2.44 g ofmalonic acid and 3.54 g of ammonium acetate (1:1.1:2.3), in 200mLof the 1-butanol was refluxed for 1.5-2 h until the evolution of CO2ceased. The precipitate formed was filtered and washed withboiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and100mL of water. Precipitates were dried at 80-100 °C for 8-10 h.Purity of product was checked by TLC, and yield obtained about65-80percent in each reaction.General procedure: Benzaldehyde (1 equiv), propanedioic acid (2 equiv) and ammonium acetate (2 equiv) were added to the solution of anhydrous ethanol (30 mL) and heated to 78 °C for 17 h. A lot of precipitated solid was filtered and dried in vacuo at 40 °C for 24 h to give a light white solid.

Molecular Weight:199.63
XLogP3:-0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:199.0400063
Monoisotopic Mass:199.0400063
Topological Polar Surface Area:63.3
Heavy Atom Count:13
Complexity:179
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes