Chemical Properties
White Solid
Uses
D-Serine Methyl Ester Hydrochloride (cas# 5874-57-7) is a compound useful in organic synthesis.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
General procedure for the synthesis of D-serine methyl ester hydrochloride from methanol and D-serine:
4.2.1.1 Synthesis of methyl (R)-2-isopropyl-4,5-dihydrooxazole-4-carboxylate
First, sulfoxide chloride (SOCl, 7.60 mL, 104.2 mmol) was slowly added dropwise to a methanolic solution of D-serine (10.0 g, 95.1 mmol) and the reaction mixture was stirred for 24 h at room temperature. After completion of the reaction, the solvent was removed by rotary evaporator to give a white solid. The solid was washed with hexane (3 x 25 mL) to give D-serine methyl ester hydrochloride (14.4 g, 97% yield) as a colorless solid. The product was characterized by 1H NMR (300 MHz, DO) with the following chemical shifts: δ 4.32-4.28 (1H, m, CH), 4.12 (1H, dd, J = 4.2, 12.5 Hz, CHaHbOH), 4.02 (1H, dd, J = 3.4, 12.5 Hz, CHaHbOH), 3.88 (3H, s, CH) .
References
[1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 372 - 376
[2] Heterocyclic Communications, 2005, vol. 11, # 3-4, p. 343 - 346
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5716 - 5726
[4] Chemical Communications, 2016, vol. 52, # 55, p. 8612 - 8614
[5] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10162 - 10165
