N-boc Asp(OH)Ome Chemical Properties

Melting point:

79-81℃

Boiling point:

407.1±40.0 °C(Predicted)

Density 

1.209

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.09±0.19(Predicted)

form 

Solid

color 

White to Almost white

Safety Information

HS Code 

2924.19.8000

N-boc Asp(OH)Ome Usage And Synthesis

Uses

N-Boc-L-aspartic acid 1-methyl ester is used as an intermediate in the preparation of modified alfa-amino acids and 5-cis-alkylprolines.

Synthesis

Boc-L-aspartyl (OBn)(OMe)14 (5.88 g, 17.43 mmol) was dissolved in methanol (20 mL) in a 50 mL round-bottomed flask and 10% palladium carbon catalyst was added under nitrogen protection. The reaction system was replaced three times with nitrogen and then three times with hydrogen. Subsequently, the reaction mixture was stirred under hydrogen atmosphere and atmospheric pressure for 6 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford the target product (S)-3-((tert-butoxycarbonyl)amino)-4-methoxy-4-oxobutanoic acid (Compound 15) in the form of a colorless gel (4.1 g, 95% yield). The specific optical rotation [α]21D of the product was 34 (c 0.1, CHCl3).1H NMR (CDCl3, 400 MHz) δ: 1.43 (s, 9H), 2.83-2.86 (d, 1H, J = 16.92 Hz), 3.01-3.05 (d, 1H, J = 16.68 Hz), 3.74 (s, 3H), 4.57 (s , 1H), 5.55-5.57 (d, 1H, J = 8.12 Hz), 10.45 (s, 1H).13C NMR (CDCl3, 100 MHz) δ: 28.3, 36.6, 49.7, 52.8, 80.5, 155.5, 171.5, 176.0. IR (KBr) ν: 3366, 2980, 1719 , 1506, 1440, 1395, 1368, 1222, 1165, 1060, 1008, 864, 764, 587 cm-1.

References

[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1459 - 1465
[2] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2274 - 2276
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 1, p. 15 - 20
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 2, p. 586 - 590
[5] Carbohydrate Research, 2013, vol. 382, p. 36 - 42

N-boc Asp(OH)Ome(98045-03-5)Related Product Information

• BOC-ARG(MTS)-OH
• BOC-CYS(ACM)-OH
• Boc-L-aspartic acid 4-Methyl ester dicyclohexylaMMoniuM salt
• BOC-CYS(ACM)-ONP
• Boc-Arg(Mts)-OH
• BOC-ASP(OFM)-OH
• BOC-CYS(TBU)-OH
• Boc-Asp-OH