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H-ASP(OTBU)-OTBU HCL

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H-ASP(OTBU)-OTBU HCL Basic information

Product Name:
H-ASP(OTBU)-OTBU HCL
Synonyms:
  • L-ASPARTIC ACID DI-T-BUTYL ESTERHYDROCHL ORIDE CRYS
  • L-ASPARTIC ACID-1,4-DI-TERT-BUTYL ESTER HYDROCHLORIDE
  • H-Asp(Obut)-Obut hydrochloride
  • H-ASP(OBUT)-OBUT·HCL
  • H-L-Asp(OtBu)-OtBu·HCl
  • L-Aspartic acid, bis(1,1-dimethylethyl) ester, hydrochloride
  • 2-aminobutanedioic acid ditert-butyl ester hydrochloride
  • L-Aspartic acid di-tert-butyl ester HCl
CAS:
1791-13-5
MF:
C12H24ClNO4
MW:
281.78
Product Categories:
  • Amino Acids
  • Aspartic acid [Asp, D]
  • Amino Acids and Derivatives
  • Amino Acid Derivatives
  • A - H
  • Amino Acids
  • Modified Amino Acids
  • Amino Acids Derivatives
Mol File:
1791-13-5.mol
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H-ASP(OTBU)-OTBU HCL Chemical Properties

Melting point:
152-155 °C
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
soluble in Methanol
form 
Solid
color 
White to Almost white
optical activity
10.6596°(C=1.0045g/100ml ETOH)
BRN 
5652807
InChIKey
GVLZIMQSYQDAHB-QRPNPIFTSA-N
CAS DataBase Reference
1791-13-5
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Safety Information

WGK Germany 
3
10-21
HS Code 
29224999

MSDS

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H-ASP(OTBU)-OTBU HCL Usage And Synthesis

Chemical Properties

White powder

Uses

L-Aspartic acid di-tert-butyl ester hydrochloride may be used in neurological comparison studies with structurally similar compounds such as L-Glutamic acid di-tert-butyl ester.

Biochem/physiol Actions

L-Aspartic acid di-tert-butyl ester hydrochloride may be used in neurological comparison studies with structurally similar compounds such as L-Glutamic acid di-tert-butyl ester (G7501).

Synthesis

42417-76-5

1791-13-5

General procedure for the synthesis of di-tert-butyl (S)-2-aminosuccinate hydrochloride from Cbz-Asp(OtBu)-OtBu 18: Pd/C (10%, 830 mg, 10% w/w) was added to an ethanol solution of Cbz-Asp(OtBu)-OtBu 18 (8.25 g, 21.8 mmol) and ammonium formate (34.3 g, 0.54 mol). ) in an ethanol solution (20 mL). The suspension was stirred overnight at room temperature. Upon completion of the reaction, the suspension was filtered through diatomaceous earth and the solvent was removed under reduced pressure. The resulting residue was dissolved in ethyl acetate and the solution was cooled to 0°C. Subsequently, an ethyl acetate solution saturated with HCl was added dropwise and stirred for 15 minutes. The precipitated solid was filtered, washed with cold ethyl acetate and dried under vacuum to afford NH2-Asp(OtBu)-OtBu hydrochloride 16 (4.28 g, 17.4 mmol, 80% yield) as a white solid, which can be used in subsequent reactions without further purification.

References

[1] Tetrahedron, 2014, vol. 70, # 44, p. 8343 - 8347

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