Z-ASP-OME Chemical Properties

Melting point:

89.0 to 93.0 °C

Boiling point:

498.9±45.0 °C(Predicted)

Density 

1.304±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.09±0.19(Predicted)

color 

White to Almost white

BRN 

4813538

CAS DataBase Reference

4668-42-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/22-37-41

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

Z-ASP-OME Usage And Synthesis

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of (S)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acid from methanol and Z-aspartic anhydride was as follows: 49.0 g (196 mmol) of benzyl (S)-(2,5-dioxo-tetrahydrofuran-3-yl)carbamate obtained from Steps 1-1 (2) was dissolved in 100 mL of ethyl acetate, followed by adding 150 mL of methanol and the reaction was stirred at room temperature for 5 hours. Upon completion of the reaction, the mixture was concentrated to dryness under reduced pressure and the resulting residue was dissolved in 200 mL of diisopropyl ether. 34 mL of dicyclohexylamine was added slowly and dropwise with stirring to produce (S)-3-((benzyloxycarbonyl)amino)-4-methoxy-4-oxobutanoic acid dicyclohexylamine salt. The salt was collected by filtration and suspended in 200 mL of distilled water. 200 mL of ethyl acetate was added and the pH was adjusted with 6N hydrochloric acid to 2. After phase separation was carried out, the organic layer was washed several times with distilled water, dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. To the concentrated residue 200 mL of diethyl ether and 20 mL of petroleum ether were added to promote crystallization. The resulting crystals were filtered to give 32.3 g of (S)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acid in 54% yield. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.37 (m, 5H), 5.76 (d, 1H), 5.13 (s, 1H), 4.65 (m, 1H), 3.76 (s, 2H), 3.00 (dd, 2H).

References

[1] Patent: WO2012/148246, 2012, A2. Location in patent: Page/Page column 13

Z-ASP-OME(4668-42-2)Related Product Information

• Z-ASP(OME)-OH,CBZ-ASP(OME)-OH
• N-Carbobenzyloxy-L-aspartic acid
• N-Benzyloxycarbonyl-L-asparagine
• N-Cbz-L-Aspartic acid 4-tert-butyl ester
• Z-ASP-OBZL
• Z-DEVD-CMK
• Z-Asp(OtBu)-OH·H2O
• Z-Asp(OtBu)-Glu(OtBu)-OH
• Z-ASP(OBZL)-OSU
• N-Cbz-L-Aspartic acid 4-benzyl ester
• Z-ASP(OTBU)-BROMOMETHYLKETONE
• Z-ASP(OTBU)-OH DCHA
• Z-Asp(OtBu)-His(Trt)-OH
• Z-ASP(OTBU)-OSU
• Z-Asp(OMe)-OtBu
• Z-TLE-OH DCHA
• Z-L-METHIONINE METHYL ESTER
• Z-TRP-ONP