Z-ASP(OME)-OH Chemical Properties

Melting point:

98 °C

Boiling point:

503.6±50.0 °C(Predicted)

Density 

1.304±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

3.63±0.23(Predicted)

color 

White

BRN 

6279422

InChIKey

PHMBNDDHIBIDRQ-JTQLQIEISA-N

CAS DataBase Reference

3160-47-2(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

Z-ASP(OME)-OH Usage And Synthesis

Chemical Properties

White powder

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

30.5 g (207 mmol) (S)-2-Amino-4-methoxy-4-oxobutanoic acid was dissolved in 726 mL of distilled water and 260 mL of ether was added. Subsequently, 40.15 g (290 mmol) of potassium carbonate was added and stirred until completely dissolved, then 41.5 mL (290 mmol) of benzyl chloroformate was slowly added. The reaction mixture was stirred continuously for 4 hours at room temperature. After completion of the reaction, phase separation was carried out and the organic layer was discarded. The aqueous layer was washed several times with ether and the pH was subsequently adjusted with 1 N hydrochloric acid to 1. The aqueous layer was again extracted several times with ether, the organic layers were combined and dried over magnesium sulfate. Finally, 55 g of (2S)-4-methoxy-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid was obtained by vacuum concentration in 94% yield. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 8.23 (s, 1H), 7.35 (m, 5H), 5.87 (d, 1H), 5.12 (s, 2H), 4.69 (m, 1H), 3.68 (s, 3H), 2.97 (dd, 2H).

References

[1] European Journal of Organic Chemistry, 2003, # 17, p. 3387 - 3397
[2] Patent: WO2012/148246, 2012, A2. Location in patent: Page/Page column 16
[3] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253
[4] Journal of Organic Chemistry, 2009, vol. 74, # 11, p. 4177 - 4187
[5] Tetrahedron Asymmetry, 2011, vol. 22, # 20-22, p. 1849 - 1854

Z-ASP(OME)-OH(3160-47-2)Related Product Information

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• Z-ASP(OTBU)-OH DCHA
• N-Cbz-L-Aspartic acid 4-tert-butyl ester
• Z-ASP-OME
• N-Carbobenzyloxy-L-aspartic acid
• Z-Asp(OtBu)-Glu(OtBu)-OH
• Z-Asp(OtBu)-His(Trt)-OH
• Z-DEVD-CMK
• Z-Asp(OtBu)-OH·H2O
• Z-ASP(OTBU)-BROMOMETHYLKETONE
• Z-ASP-OBZL
• Z-ASP(OSU)-OBZL
• Z-Asp(OMe)-OtBu
• Z-ASP(OTBU)-OME
• Z-ASP(OTBU)-ONP
• Z-ASP(OTBU)-OSU
• Z-ASP(ONP)-OBZL
• Z-ASP(OBZL)-OSU