Uses
L-Aspartic acid 4-methyl ester is a protected form of L-Aspartic acid. L-Aspartic acid is a nonessential amino acid that is used to biosynthesize other amino acids within the human body. L-Aspartic acid also increases membrane conductance of mammalian neurons by voltage-dependent means, causing depolarization and nerve impulses that travel to key areas of the central nervous system.
Synthesis
At -10°C, 5 g of L-aspartic acid (37.6 mmol) was slowly added to 26 mL of anhydrous methanol solution containing 3.8 mL (41.2 mmol) of SOCl? The reaction mixture was stirred continuously at room temperature for 2 h. Subsequently, 75 mL of diethyl ether was added to promote precipitation of the product. The resulting white solid was collected by filtration and washed with 2 x 50 mL of diethyl ether to give the final (S)-aspartic acid-β-methyl ester hydrochloride in 85% yield. The product was a white solid.1H NMR (300 MHz, DMSO) characterized the data as follows: δ (ppm) = 3.05 (dd, J = 3.4,4.7 Hz, 2H, CH?), 3.78 (s, 3H, OCH?), 4.31-4.35 (m, 1H, CHN).
References
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 833 - 834
[2] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 1900 - 1903
[3] Patent: WO2013/30193, 2013, A1. Location in patent: Paragraph 30
[4] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4982 - 4984
[5] Chemical Communications, 2001, # 18, p. 1710 - 1711
