BOC-L-Asparagine Chemical Properties

Melting point:

175 °C (dec.)(lit.)

Boiling point:

374.39°C (rough estimate)

Density 

1.2896 (rough estimate)

refractive index 

-7 ° (C=1, DMF)

Flash point:

245°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

almost transparency in N,N-DMF

form 

Powder or Crystalline Powder

pka

3.79±0.10(Predicted)

color 

White

optical activity

[α]20/D 7.8±0.5°, c = 2% in DMF

BRN 

1977963

InChI

InChI=1S/C9H16N2O5/c1-9(2,3)16-8(15)11-5(7(13)14)4-6(10)12/h5H,4H2,1-3H3,(H2,10,12)(H,11,15)(H,13,14)/t5-/m0/s1

InChIKey

FYYSQDHBALBGHX-YFKPBYRVSA-N

SMILES

C(O)(=O)[C@H](CC(N)=O)NC(OC(C)(C)C)=O

CAS DataBase Reference

7536-55-2(CAS DataBase Reference)

EPA Substance Registry System

L-Asparagine, N2-[(1,1-dimethylethoxy)carbonyl]- (7536-55-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

TSCA 

Yes

HS Code 

2924 19 00

HazardClass 

IRRITANT

MSDS

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

BOC-L-Asparagine Usage And Synthesis

Chemical Properties

WHITE AMORPHOUS POWDER

Uses

Nα-Boc-L-asparagine is an N-Boc-protected form of L-Asparagine (A790005). L-Asparagine was first isolated by Robiquet and Vauquelin from asparagus juice (a high source of L-asparagine). L-Asparagine is often incorporated into proteins, and is a basis for some cancer therapies as certain cancerous cells require L-asparagine for growth.

Definition

ChEBI: The Nalpha-t-butoxycarbonyl derivative of L-asparagine

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

L-asparagine (15 g, 0.113 mol, 1.0 eq.) and sodium carbonate (12 g, 0.113 mol, 1.0 eq.) were dissolved in a solvent mixture of water (225 mL) and 1,4-dioxane (225 mL) at room temperature. To this solution was slowly added di-tert-butyl dicarbonate (30 g, 0.137 mol, 1.2 eq.) and the reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, 1,4-dioxane was removed by distillation under reduced pressure. Subsequently, the pH of the solution was adjusted to 2 with 37% hydrochloric acid, at which point a white solid precipitated. The solid product was collected by filtration, washed with water and dried under appropriate conditions. Finally, 24 g of BOC-L-asparagine was obtained in 91% yield. The product characterization data were as follows: melting point 175°C-180°C (literature value 175°C); 1H NMR (DMSO-D6) δ 12.5 (1H, br); 7.31 (1H, br); 6.91 (1H, br); 6.87 (1H, d, J=8.4 Hz); 4.23 (1H, q, J=7.7 Hz); 2.56- 2.36 (2H, m); 1.38 (9H, s).

References

[1] Patent: WO2005/21558, 2005, A2. Location in patent: Page/Page column 214
[2] Patent: US2006/189806, 2006, A1. Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1185 - 1208
[4] Angewandte Chemie - International Edition, 2007, vol. 46, # 14, p. 2470 - 2477
[5] Organic Syntheses, 1985, vol. 63, p. 160 - 160

BOC-L-Asparagine(7536-55-2)Related Product Information

• L-Asparagine
• ASPARAGINASE
• D-(-)-Asparagine monohydrate
• Di-tert-butyl dicarbonate
• PYRAZOPHOS
• 2-Chloro-2-methylpropane
• 1,1'-Carbonyldiimidazole
• FMOC-ASN(TRT)-OPFP
• DI-TERT-BUTYL ETHER
• Carbonyl iron powder
• NICKEL CARBONYL
• N-BOC-L-ASPARAGINE(XANTHYL)
• BOC-L-ASPARAGINE(TRITYL)
• BOC-ASP-OH
• NALPHA-BOC-D-ASPARAGINE,N-ALPHA-T-BOC-D-ASPARAGINE,BOC-D-ASPARAGINE,N-BOC-D-ASPARAGINE,NA-T-BOC-D-ASPARAGINE
• DDZ-ASN-OH
• BOC-L-ASPARAGINE BENZYL ESTER
• BOC-L-ASPARAGINE N-HYDROXYSUCCINIMIDE ESTER