3-Amino-3-(4-methylphenyl)propionic acid

white to off-white granular or crystalline powder

To 250 mL of ethanol were added 50.0 g (0.42 mol) of 4-tolylaldehyde, 47.6 g (0.46 mol) of malonic acid and 64.2 g (0.83 mol) of ammonium acetate, and the mixture was reacted while stirring under reflux (80 to 90°C) for 7.5 hours. The obtained reaction mixture was stirred at 0 to 5°C for 30 minutes and then filtered to give 51.4 g of 3-amino-3-(4-tolyl)propionic acid (racemic mixtures) (isolation yield based on 4-tolylaldehyde: 68.9percent) as white powder. Incidentally, physical properties of the 3-amino-3-(4-tolyl)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.EXAMPLE 6 (R)-3- (3-Biphenyl-4-yl-ureido)-N (2-pyrrolidin-1-yl-ethyl)-3-p-tolyl-propionamide. A. 3- (3-Biphenvl-4-vl-ureido)-3-p-tolyl-propionic acid. To a solution of 3-amino- 3-(p-tolyl) propionic acid (0.50 g, 2.79 mmol) and TEA (0. 26 g, 2.56 mmol) in CH2CI2 (28 mL) cooled to 0 C, was added 4-isocyanato-biphenyl (0.55 g, 2.79 mmol). The mixture was stirred at 0 C for 30 min and was then brought to rt and stirred for an additional 3 h. The solvent was removed, water (20 mL) was added to the clear residue, and the mixture was then chilled to 0 C and acidified using 1 N HCI. The resulting precipitate was collected by filtration, washed with copious amounts of H20, and dried under vacuum to afford 0.87 g (83%) of the desired product as a white solid. MS (electrospray) : mass calculated for C23H22N203, 374.16 ; m/z found, 413.0 [M+Na] +.'H NMR (400 MHz, DMSO-d6) : 8.74 (s, 1 H), 7.65-7. 29 (m, 9H), 7.25 (d, J= 8.1 Hz, 2H), 7.14 (d, J = 7.9 Hz, 2H), 6.64 (d, J= 8.5 Hz, 1 H), 5. 11-5. 06 (m, 1 H), 2.74-2. 67 (m, 2H), 2.27 (s, 3H).

Molecular Weight:179.22
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:179.094628657
Monoisotopic Mass:179.094628657
Topological Polar Surface Area:63.3
Heavy Atom Count:13
Complexity:174
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes