Uses
Boc-L-serine methyl ester is a derivative of L-Serine Methyl Ester Hydrochloride (S271005) derivative. Boc-L-serine methyl ester is an amino acid derivative used in the preparation of Tn antigen, L-glutamic acid p-nitroanilide analogs and new biomedical polymers having Serine and Threonine side groups.
Synthesis
General procedure for the synthesis of Boc-L-serine methyl ester from di-tert-butyl dicarbonate and L-serine methyl ester hydrochloride: crude L-serine methyl ester hydrochloride (0.29 mol) was suspended in dichloromethane (200 mL), followed by the addition of triethylamine (79 mL, 0.57 mol) and di-tert-butyl dicarbonate (68 g, 0.31 mol) to the mixture. The reaction was carried out at 0°C. After removal of the cooling bath, the reaction mixture was stirred at room temperature overnight and then diluted with methyl tert-butyl ether (300 mL). The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by fast column chromatography on silica gel to afford Boc-L-serine methyl ester (60 g, 94% yield) as a colorless oil.
References
[1] European Journal of Organic Chemistry, 2000, # 1, p. 115 - 124
[2] Organic Letters, 2003, vol. 5, # 24, p. 4599 - 4602
[3] Journal of Organic Chemistry, 2015, vol. 80, # 1, p. 40 - 51
[4] Journal of the American Chemical Society, 2016, vol. 138, # 43, p. 14218 - 14221
[5] Organic and Biomolecular Chemistry, 2013, vol. 11, # 19, p. 3089 - 3093
