Boc-L-aspartic acid 4-methyl ester Chemical Properties

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Solution

color 

Clear colorless to yellow

BRN 

4810472

CAS DataBase Reference

59768-74-0(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

Boc-L-aspartic acid 4-methyl ester Usage And Synthesis

Chemical Properties

White solid

Uses

Boc-L-aspartic Acid β-Methyl Ester is used to prepare isoxazoline glycoprotein IIb/IIIa antagonists. It is also used to synthesize glutamic acid analogs as potent inhibitors of leukotriene A4 hydrolase.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

3.74 g (20.5 mmol) of L-aspartic acid-β-methyl ester hydrochloride was dissolved in 85 mL of mixed dioxane/H2O (2:1) solvent and 2.21 g (20.8 mmol) of Na2CO3 was added at 0 °C. After the reaction was carried out for 30 min, 2.21 g (20.8 mmol) of Na2CO3 and 5 g (25.7 mmol) di-tert-butyl dicarbonate (Boc2O) and stirred at room temperature overnight. After completion of the reaction, the solvent was removed by vacuum concentration and the residue was poured into 60 mL of ice water. The aqueous layer was washed with ether (2 × 25 mL), followed by acidification with 100 mL of 1 M NaHSO4 to pH = 3, and then the aqueous layer was extracted with ether (3 × 75 mL). The organic layers were combined, dried with MgSO4, filtered and the solvent evaporated, and the residue was purified by column chromatography using ethyl acetate as eluent to afford the target product 2-(S)-(tert-butoxycarbonylamino)-(methoxycarbonyl)butanoic acid (Boc-L-aspartic acid 4-methyl ester) in 75% yield. The product was a white solid with an Rf value of 0.50 (ethyl acetate) and [α]D=+28.6 (c=0.3; CHCl3).IR (cm-1): 3429 (NH), 2979 (CH), 1714 (C=O), 1509, 1438, 1394, 1367, 1156, 1057, 1026, 843, 780, 734 .1H NMR (300 MHz, CDCl3): δ (ppm) = 1.42 (s, 9H, CH3), 2.82 (dd, J=4.8,17.2 Hz, 1H, CH2), 3.02 (dd, J=17.2,4.1 Hz, 1H, CH2), 3.69 (s, 3H, OCH3), 4.59-4.62 (m 1H, CHN), 5.57 (d, J=8.5Hz, 1H, NHBoc), 10.8 (sl, 1H, COOH).13C NMR (75MHz, CDCl3): δ (ppm) = 28.2 (CH3), 36.4 (CH2), 49.7 (CHN), 52.1 (OCH3), 80.5 (C(CH3)3 ), 155.6 (COO), 171.6 (COO), 175.8 (COO). Elemental analysis (C10H17NO6) calculated values: C 48.58, H 6.93, N 5.67; measured values: C 48.64, H 7.04, N 5.68.

References

[1] Heterocycles, 1997, vol. 46, # 1, p. 335 - 348
[2] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 1900 - 1903
[3] Chemical Communications, 2001, # 18, p. 1710 - 1711
[4] Patent: WO2013/30193, 2013, A1. Location in patent: Page/Page column 30; 31
[5] RSC Advances, 2015, vol. 5, # 88, p. 71868 - 71872

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