BENZOTRIAZOL-1-YL-BENZYLOXYCARBONYLAMINO-ACETIC ACID

To a 250 ml. flask equipped mechanical stirring, was added 2-oxoacetic acid hydrate (9.2 g, 0.1 mol), benzyl carbamate (15.1 g, 0.1 mol) and 1H-benzo[dj[1, 2, 3jtriazole (9.2 g, 0.1 mol), and toluene (300 mL). The resulting solution was stirred for 2 h at 120 °C in an oil bath. The resulting mixture was filtered and the solid residue was washed with petroleum ether (3x), and dried in vacuo to give 2-(1H-benzo[dj[1, 2, 3jtriazol-1-yl)-2-(benzyloxycarbonylamino)aceticacid (28.6 g, 87percent) as a white solid that was used without further purification. ESI-MS m/z:327 [M+HfTo a 250 mL flask equipped mechanical stirring, was added 2-oxoacetic acid hydrate (9.2 g, 0.1 mol), benzyl carbamate (15.1 g, 0.1 mol) and 1H-benzo[d][1, 2, 3]triazole (9.2 g, 0.1 mol), and toluene (300 mL). A mixture of benzyl carbamate (82.1 g, 0.54 mol), glyoxylic acid monohydrate (50 g, 0.54 mol) and benzotriazole (64.7 g, 0.54 mol) in toluene (2.5 L) was heated at reflux with Dean and Stark water removal for 2 hours. A total of 23 mL of water was collected during the first hour before water evolution ceased. The mixture was allowed to cool to room temperature and the resulting solid filtered and washed with diethyl ether (200 mL). The damp filter cake was dried at 40 °C/50 mmHg overnight to give a cream coloured powder (134.9 g).

Molecular Weight:326.31
XLogP3:2.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:326.10150494
Monoisotopic Mass:326.10150494
Topological Polar Surface Area:106
Heavy Atom Count:24
Complexity:455
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes