N-(DIPHENYLMETHYLENE)GLYCINEMETHYLESTER

Off-White to Pale Yellow Solid

To a stirring solution of glycine methyl ester hydrochloride (17.49 g, 139 mmol) in dry dichloromethane (150 mL) under N2 at room temperature was added diphenylimine (25.00 g, 137 mmol) in one portion. The reaction mixture was stirred for 24 h, during which time ammonium chloride precipitated. Water (20 mL) was added and the layers were separated. The organic layer was washed with saturated Na2CO3 solution (2 x 20 mL) and brine (20 mL). The organic layer was dried (Na2SO4), filtered and concentrated by rotary evaporation to give ~ 35 g of a thick light brown syrup (99 percent pure) in ~ 100 percent yield. This was taken on to the next reaction without further purification. To a stirring solution of methyl glycine ester hydrochloride (17.49 g, 139 mmol) in dry dichloromethane (150 mL) under N2 at room temperature was added diphenylimine (25.00 g, 137 mmol) in one portion. The reaction mixture was stirred for 24 h, during which time ammonium chloride precipitated. Water (20 mL) was added and the layers were separated. The organic layer was washed with saturated Na2C03 solution (2 x 20 mL) and brine (20 mL). The organic layer was dried (Na2SC>4), filtered and concentrated by rotary evaporation to give ~35 g of a thick light brown syrup (99percent pure) in ~ 100percent yield. This was taken on to the next reaction without further purification.Benzophenone imine (50.0 g, 0.276 mol) was added in one batch to a solution of glycine methyl ester hydrochloride (39.4 g, 0.314 mol) in 300 mL dichloromethane under stirring, and the resulting reaction solution was stirred at room temperature for 1 day. To a stirred suspension containing 5.00 g (39.9 mmol) of glycine methyl ester hydrochloride in 20 mL of anhydrous CH[0067] Methyl 2-(diphenylmethyleneamino)acetate (41). To a stirred suspension containing 5.00 g (39.9 mmol) of glycine methyl ester hydrochloride (40) in 20 mL of anhydrous CH

Molecular Weight:253.29
XLogP3:3.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:253.110278721
Monoisotopic Mass:253.110278721
Topological Polar Surface Area:38.7
Heavy Atom Count:19
Complexity:293
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes