Acetamide, N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-

Synthesis

General procedure for the synthesis of (S)-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide from L-phenylalaninol and ethanoic anhydride: L-phenylalaninol (1 mmol) was mixed with ethanoic anhydride (1.2 mmol) in a 50 mL round-bottomed flask and the reaction was stirred at room temperature until complete (monitored by TLC). After completion of the reaction, the mixture was dissolved in ether (5 mL) and allowed to stand at room temperature for 1 hour. During this time, the product (S)-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide precipitated as crystals, which were collected by filtration. For the reaction of solid substrates (e.g., sulfonamides), the same operating procedure is used, but the solubility of the mixture is adjusted with water.The N-acylated sulfonamide product is obtained by crystallization from diethyl ether.

References

[1] Chinese Chemical Letters, 2010, vol. 21, # 2, p. 155 - 158
[2] Oriental Journal of Chemistry, 2015, vol. 31, # 2, p. 913 - 919
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 10, p. 2742 - 2755
[4] Patent: US6750348, 2004, B1. Location in patent: Page column 47
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2216 - 2220