CBZ-BETA-AMINO-D-ALANINE has been reported in the literature to be prepared by reacting N-benzyloxycarbonyl-D-asparagine with iodoacetic acid phenyl diacetate.
At ambient temperature, N-benzyloxycarbonyl-D-asparagine (5.0 g) was added to a stirred solution of iodoacetic acid phenyl diacetate (7.26 g) in a mixture of ethyl acetate (44 ml), acetonitrile (44 ml), and water (22 ml). After stirring for 3 hours, the reaction mixture was cooled to 50°C and then stirred for 2 hours. The insoluble matter was collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give N(α)-ZD-2,3-diaminopropionic acid, a white solid, with a yield of 4.15 g. IR (KBr) : 3303.5, 3027.7, 2948.6, 1693.2, 1656.5, 1623.8, 1592.9, 1542.8 cm-1 .1HNMR (D2O-TFA, δ ) : 3.35 (1H, dd, J=13.4 and 8.7Hz), 3.57 (1H, dd, J=13.4 and 5.3Hz), 4.57 (1H, dd, J=8.7 and 5.3Hz), 5.16 (2H, s), 7.43 (5H, s) MASS (m/z) : 239 (M+H)+ mp : 238°C (dec.) [α ]D31 : 8.6° (c=1.0, 1N NaOH aq.)
