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L-Aspartic acid 4-benzyl ester

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L-Aspartic acid 4-benzyl ester Basic information

Product Name:
L-Aspartic acid 4-benzyl ester
Synonyms:
  • H-ASP(OBZL)-OH
  • H-L-ASP(OBZL)-OH
  • L-ASPARTIC ACID 4-BENZYL ESTER
  • L-ASPARTIC ACID BETA-BENZYL ESTER
  • ASPARTIC ACID(OBZL)-OH
  • BETA-BENZYL L-ASPARTATE
  • benzyl hydrogen beta-L-aspartate
  • Asp(OBz)-OH
CAS:
2177-63-1
MF:
C11H13NO4
MW:
223.23
EINECS:
218-541-8
Product Categories:
  • Amino Acids Derivatives
  • Aspartic acid [Asp, D]
  • Amino Acids and Derivatives
  • Amino Acids
  • alpha-Amino Acids
  • Amino Acid Benzyl Esters
  • Amino Acids (C-Protected)
  • Biochemistry
  • AMINOACIDS DERIVATIVES
Mol File:
2177-63-1.mol
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L-Aspartic acid 4-benzyl ester Chemical Properties

Melting point:
~225 °C (dec.)
Boiling point:
413.1±45.0 °C(Predicted)
Density 
1.283±0.06 g/cm3(Predicted)
refractive index 
27 ° (C=1, 1mol/L HCl)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
pka
2.16±0.23(Predicted)
form 
Powder
color 
White
Water Solubility 
Insoluble in water.
BRN 
1983183
CAS DataBase Reference
2177-63-1(CAS DataBase Reference)
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Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
HS Code 
29242990

MSDS

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L-Aspartic acid 4-benzyl ester Usage And Synthesis

Chemical Properties

Crystalline

Uses

L-Aspartic acid β-benzyl ester is used in the synthesis of peptides with a 1,4-diazepine-2,5-dione ring structure and in development of block copolymers.

Definition

ChEBI: L-aspartic acid beta-benzyl ester is an aspartic acid derivative.

Synthesis

56-84-8

100-51-6

2177-63-1

100 mL of anhydrous ether was added to a 500 mL beaker and 20 mL of concentrated sulfuric acid was added slowly and dropwise while stirring and cooling to room temperature. Subsequently, 150 mL of benzyl alcohol was added and the ether was removed by stirring well. Under reduced pressure, 26 g of L-aspartic acid was added to the reaction flask in 5 batches. The reaction was stirred for 24 h at room temperature, after which 300 mL of 95% ethanol was added, and 80 mL of pyridine was slowly added dropwise through a dropping funnel with vigorous stirring while dropping. The reaction mixture was placed in a refrigerator overnight and the solid was collected by filtration. The solid was dissolved with 80% ethanol with stirring, heated and filtered. The filtrate was frozen for 8 hours, filtered again and finally lyophilized to obtain pure β-aspartic acid benzyl ester in 90% yield.

References

[1] Journal of Natural Products, 2017, vol. 80, # 7, p. 2136 - 2140
[2] Patent: CN107129501, 2017, A. Location in patent: Paragraph 0009; 0010; 0011
[3] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 5, p. 459 - 464
[4] Patent: US2004/133033, 2004, A1. Location in patent: Page 4-5
[5] Chemistry - A European Journal, 2018, vol. 24, # 54, p. 14373 - 14377

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