Nitrogen → HCID 23456069, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of tert-butoxycarbonylamino-acetic acid (906 mg, 5.12 mmol) in CH2Cl2 (27.0 mL) was treated at 0° C. with HOBt (777 mg, 5.64 mmol), DCC (1.17 g, 5.64 mmol) N-methylmorpholine (0.85 mL, 7.68 mmol) and 2-amino-3-hydroxy-3-phenyl-propionic acid methyl ester (1.00 g, 5.12 mmol). The resulting mixture was stirred at rt for 2 h, poured in 5% KHSO4 (100 mL), stirred for 15 min, filtered and washed with CH2Cl2. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were washed with sat. aq. NaHCO3, brine, dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC(CH2Cl2 to 99:1 CH2Cl2-MeOH) gave the title compound as a white solid. TLC: rf (90:10 CH2Cl2-MeOH)=0.48. LC-MS-conditions 02: tR=0.85 min, [M+H]+=353.05.

Provenance & Evidence