L-Phenylalanine benzyl ester hydrochloride

Chemical Properties

White crystal

Uses

L-Phenylalanine Benzyl Ester Hydrochloride is a commonly used reactant for the synthesis of L-isoserine derivatives as aminopeptidase N inhibitors and PF-04449913 as a potent and orally bioavailable inhibitor of smoothened.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of L-phenylalanine benzyl ester hydrochloride from (S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropionate was as follows: benzyl (2S)-2-(tert-butoxycarbonylamino)-3-phenylpropionate (12.8 g, 36 mmol) was dissolved in an ether solution of 2 M HCl (90 mL) and a dioxane solution of 4 M HCl (18 mL). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was diluted with hexane (100 mL) and subsequently filtered to afford L-phenylalanine benzyl ester hydrochloride (7.98 g, 76% yield) as a white fine powder. The product was characterized by 1H NMR (CD3OD, 400 MHz): δ (ppm) 7.40-7.15 (m, 10H), 5.23 (s, 2H), 4.36-4.31 (m, 1H), 3.26-3.12 (m, 2H).

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4235 - 4243
[2] Patent: US9441012, 2016, B2. Location in patent: Page/Page column 67
[3] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 14, p. 1497 - 1499
[4] Journal of Enzyme Inhibition and Medicinal Chemistry, 2012, vol. 27, # 2, p. 302 - 310
[5] Chemistry - A European Journal, 2012, vol. 18, # 21, p. 6528 - 6541