N-Cbz-L-threonine is an N-Cbz-protected form of L-Threonine (T405500). L-Threonine is an essential amino acid that is commonly used as a feed and food additive. L-Threonine is produced in mass quantities by mutant Escherichia coli strains for research and food nutrition purposes. L-Threonine can be naturally found in fish and poultry, and is incorporated in some important proteins in the human body (such as hemoglobin and insulin).
Add L-Thr (30 mmol), 50 mL of cooled saturated Na2CO3 solution in a 250 mL reaction vial, dissolve with ice bath stirring; drop 20 mL of acetone solution of Z-OSu (39.4 mmol) into the reaction vial; stir the reaction at 25C, and monitor the progress of the reaction by TLC-ultraviolet fluorescence and ninhydrin colorimetry. At the end of the reaction, H2O was added.
After the reaction, add H2O , extract with Et2O(30mL2) at pH>9, collect the aqueous phase, adjust the pH to 3~4 with 1.5NHCl, extract with EtOAc(30mL3), merge the organic phases, wash with saturated NaCl solution(25mL2), dry with anhydrous Na2SO4, check the purity with TLC-ultraviolet fluorescence and ninhydrin colorimetric method, dry with evaporation under reduced pressure, dry in vacuum, get a light yellow color. Vacuum drying, obtained slightly yellow oily liquid N-Benzyloxycarbonyl-L-threonine, low temperature preservation.
