BOC-GLU(OBZL)-OME Chemical Properties

Melting point:

38-41 °C

Boiling point:

471.2±40.0 °C(Predicted)

Density 

1.144±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

pka

10.96±0.46(Predicted)

Appearance

White to light yellow Solid

BOC-GLU(OBZL)-OME Usage And Synthesis

Synthesis

Step 1: Iodomethane (1.01 mL, 16.3 mmol) was slowly added dropwise to a mixed solution of THF (14.82 mmol) and DMF (25 mL) of (2S)-5-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid (5.00 g) along with K2CO3 (2.25 g, 16.3 mmol). The reaction mixture was stirred at room temperature for about 3 hours before iodomethane (1.01 mL, 16.3 mmol) was added again. Subsequently, EtOAc was added to the reaction mixture and washed three times with 10% Na2S2O3 solution and then dried with MgSO4. After concentration under reduced pressure to remove the solvent, the crude product was purified by silica gel column chromatography (100:1, followed by 50:1 CHCl3/MeOH) to afford methyl (S)-5-benzyl-2-((tert-butoxycarbonyl)amino)pentanedioate (4.20 g, 12.23 mmol, 82% yield). m/z of C18H25NO6 was detected by ESIMS as 352 (M + H ).

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1899 - 1913
[2] Patent: US2008/318957, 2008, A1. Location in patent: Page/Page column 41-42
[3] Patent: WO2012/109164, 2012, A1. Location in patent: Page/Page column 39
[4] Organic and Biomolecular Chemistry, 2007, vol. 5, # 12, p. 1915 - 1923
[5] Organic Letters, 2016, vol. 18, # 9, p. 1968 - 1971

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