Boc-Asp-OH Chemical Properties

Melting point:

116-118 °C(lit.)

alpha 

-6 º (c=1, MeOH)

Boiling point:

375.46°C (rough estimate)

Density 

1.3397 (rough estimate)

refractive index 

1.4640 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.77±0.23(Predicted)

form 

Crystalline Powder

color 

White to off-white

optical activity

[α]20/D 6.0°, c = 1 in methanol

BRN 

1913973

CAS DataBase Reference

13726-67-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

2924 19 00

MSDS

• Language:English Provider:Boc-Asp-OH
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Boc-Asp-OH Usage And Synthesis

Chemical Properties

white to off-white crystalline powder

Uses

N-Boc-L-aspartic acid is an N-Boc-protected form of L-Aspartic acid (A790024). 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.

Definition

ChEBI: Nalpha-(tert-butoxycarbonyl)-l-aspartic acid is an aspartic acid derivative.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

GENERAL STEPS: In a 500 mL single-necked round-bottomed flask, L-aspartic acid (4 g, 30 mmol), 1,4-dioxane (120 mL) and deionized water (60 mL) were mixed to form a heterogeneous solution. Under continuous stirring, 1 M aqueous sodium hydroxide solution was added dropwise until the solution became homogeneous and clarified, indicating complete dissolution of L-aspartic acid. Subsequently, the reaction mixture was cooled in an ice bath and di-tert-butyl dicarbonate (7.2 g, 33 mmol) dissolved in 1,4-dioxane (20 mL) was added slowly and dropwise. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solvent was partially evaporated using a rotary evaporator until the final volume was about 30 mL. ethyl acetate (20 mL) was then added and the aqueous layer was acidified to pH 2 with aqueous potassium bisulfate under ice-bath cooling conditions. the mixture was transferred to a partitioning funnel, and the product was extracted with ethyl acetate (3 aliquots at a time). The organic layers were combined and dried with anhydrous sodium sulfate. Subsequently, the solvent was evaporated using a rotary evaporator and further dried under vacuum overnight to give BOC-L-aspartic acid as a white solid (6 g, 85% yield).1H NMR (600 MHz, DMSO-d6) data: δ 1.38 (s, 9H), 2.51-2.55 (m, 1H), 2.65-2.69 (m, 1H). 4.24-4.28 (m, 1H), 7.05-7.07 (d, 1H, J = 12 Hz), 12.5 (s, 2H).

References

[1] Journal of the American Chemical Society, 2015, vol. 137, # 51, p. 16084 - 16097
[2] Patent: US2017/168042, 2017, A1. Location in patent: Paragraph 0203-0204
[3] Asian Journal of Chemistry, 2014, vol. 26, # 15, p. 4716 - 4722
[4] Patent: EP1647283, 2006, A1. Location in patent: Page/Page column 5
[5] Chemistry Letters, 1988, # 10, p. 1643 - 1646

Boc-Asp-OH(13726-67-5)Related Product Information

• Boc-Asp-OtBu
• 4-tert-Butyl N-[(tert-butoxy)carbonyl]-L-aspartate dicyclohexylamine salt
• Boc-D-aspartic acid 4-benzyl ester
• Boc-L-aspartic acid 4-methyl ester
• Boc-D-aspartic acid 4-cyslohexyl ester
• BOC-ASP(OBZL)-OSU
• Boc-Asp(Ochx)-OH
• Boc-L-aspartic acid 4-benzyl ester
• BOC-ASP(OTBU)-OSU
• Boc-Asp-OH
• Boc-L-aspartic acid 1-benzyl ester
• Boc-L-aspartic acid 4-tert-butyl ester
• N-tert-Butoxycarbonyl-L-glutamic acid gamma-tert-butyl ester
• L-Aspartic acid
• L-ASPARTIC ACID
• BOC-D-ASP(OBZL)-OH
• BOC-D-ASP-OTBU
• BOC-D-ASP(OTBU)-OH