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L-Glutamic acid 5-tert-butyl ester

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L-Glutamic acid 5-tert-butyl ester Basic information

Product Name:
L-Glutamic acid 5-tert-butyl ester
Synonyms:
  • L-Glutamic acid γ-t.-butyl ester
  • Glu(OtBu)-OH
  • L-Glutamic acid γ-tert·butyl ester monohydrate
  • L-Glutamic acid 5-t-Butyl Ester
  • GLUTAMIC ACID GAMMA-T-BUTYL ESTER MONOHYDRATE
  • L-GLUTAMIC ACID-Y-T-BUTYL ESTER
  • L-GLUTAMIC ACID-Y-T-BUTYLESTER MONOHYDRATE
  • L-GLUTAMIC ACID .GAMMA.-TERT-BUTYL ESTER MONOHYDRATE
CAS:
2419-56-9
MF:
C9H17NO4
MW:
203.24
EINECS:
607-337-8
Product Categories:
  • Amino Acids
  • Glutamic acid [Glu, E]
  • Amino Acids and Derivatives
  • Amino Acid Derivatives
  • Glutamic Acid
  • Peptide Synthesis
Mol File:
2419-56-9.mol
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L-Glutamic acid 5-tert-butyl ester Chemical Properties

Melting point:
182°C(lit.)
Boiling point:
110 °C(Press: 0.05 Torr)
Density 
0.992 g/cm3
storage temp. 
2-8°C
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form 
Solid
pka
2.20±0.10(Predicted)
color 
White to Almost white
Water Solubility 
Sparingly soluble in water; practically insoluble in ethanol or ether.
BRN 
2049031
Major Application
peptide synthesis
InChI
InChI=1S/C9H17NO4/c1-9(2,3)14-7(11)5-4-6(10)8(12)13/h6H,4-5,10H2,1-3H3,(H,12,13)/t6-/m0/s1
InChIKey
OIOAKXPMBIZAHL-LURJTMIESA-N
SMILES
C(O)(=O)[C@H](CCC(OC(C)(C)C)=O)N
CAS DataBase Reference
2419-56-9(CAS DataBase Reference)
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Safety Information

Risk Statements 
22-24
Safety Statements 
22-24/25-25
WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
29224999
Storage Class
11 - Combustible Solids

MSDS

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L-Glutamic acid 5-tert-butyl ester Usage And Synthesis

Chemical Properties

White powder crystal

Uses

L-Glutamic acid 5-tert-butyl ester is used as a fine chemical intermediate, pharmaceutical intermediate.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

In a 3000mL three-necked flask, 2324g of tert-butyl acetate and 73.5g of glutamic acid were added, stirred, and was added dropwise. 160.8 mL of perchloric acid, react for 48 hours at 10??C, cool down to 0??C, add 1000 mL of water, extract (the remaining tert-butyl acetate was used as solvent extraction), neutralized with Na2CO3 to pH=8 to 9, partitioned, and then extracted with 400 mL of 1% Na2CO3 aqueous solution was washed three times, and the tert-butyl acetate layer was concentrated under reduced pressure to give 42 g of Glu(OtBu)2 as an oil in 32.4% yield.

In a 1000 mL three-necked flask, 42 g of Glu(OtBu)2 was added, 400 mL of water and 11 g of CuCl2 were added, . The temperature was raised to 50 ??C and the reaction was carried out for 12 h to produce Cu[Glu(OtBu)]x (x=1-2); then it was lowered to room temperature and was added 19g tetramethylethylenediamine and 100mL dioxane, and then adjust the pH to 8~9 with triethylamine to produce L-glutamic acid-5-tert-butyl ester.

L-Glutamic acid 5-tert-butyl ester Preparation Products And Raw materials

Preparation Products

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