Uses
(R)-(-)-2-Phenylglycine Methyl Ester Hydrochloride is an intermediate in the synthesis of Cephradine, a cephalosporin antibiotic. It functions as an acyl donor in the enzymatic synthetic process for cephradine synthesis.
Synthesis
Methylation reaction of L-phenylglycine. L-phenylglycine (1 g, 6.05 mmol, 1.0 eq.) was suspended in methanol (25 mL) and cooled to 0°C. Thionyl chloride (475 μL, 6.66 mmol, 1.5 eq.) was slowly added. after 10 min, the reaction mixture was heated to 75 °C and refluxed for 2 h. The reaction was completed by TLC. After completion of the reaction (monitored by TLC), the solvent was removed under vacuum to give a white solid, L-phenylglycine methyl ester hydrochloride (1.23 g, quantitative yield).
References
[1] Tetrahedron, 1999, vol. 55, # 11, p. 3337 - 3354
[2] European Journal of Organic Chemistry, 2009, # 30, p. 5185 - 5191
[3] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 649 - 660
[4] Tetrahedron, 2009, vol. 65, # 6, p. 1200 - 1206
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1992, # 8, p. 1279 - 1285
