Boc-L-glutamic acid 1-tert-butyl ester Chemical Properties

Melting point:

111.0 to 115.0 °C

Boiling point:

449.8±40.0 °C(Predicted)

Density 

1.121±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Soluble in dimethyl formamide.

form 

powder to crystaline

pka

4.48±0.10(Predicted)

color 

White to Almost white

optical activity

-30.8554° (C=1.0042 g/100ml, MEOH)

BRN 

3653769

InChI

InChI=1S/C14H25NO6/c1-13(2,3)20-11(18)9(7-8-10(16)17)15-12(19)21-14(4,5)6/h9H,7-8H2,1-6H3,(H,15,19)(H,16,17)/t9-/m0/s1

InChIKey

YMOYURYWGUWMFM-VIFPVBQESA-N

SMILES

C(OC(C)(C)C)(=O)[C@H](CCC(O)=O)NC(OC(C)(C)C)=O

CAS DataBase Reference

24277-39-2(CAS DataBase Reference)

Safety Information

Risk Statements 

22/22-36/37/38

Safety Statements 

4-7-28-35-44

WGK Germany 

3

HS Code 

2924 19 00

MSDS

• Language:English Provider:SigmaAldrich

Boc-L-glutamic acid 1-tert-butyl ester Usage And Synthesis

Chemical Properties

White powder crystal

Uses

Boc-Glu-OtBu is an N-terminal protected amino acid used in solid-phase peptide synthesis (SPPS) to make unique peptides containing glutamate tert-butyl ester residues.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of Boc-L-glutamic acid 1-tert-butyl ester from (S)-1-tert-butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate: crude N-Boc-glutamic acid 1-tert-butyl ester (5-methyl ester from the previous step, 30.4 g, 95.8 mmol) was dissolved in THF (300 mL), 1N LiOH was added aqueous solution (144 mL). The reaction mixture was stirred at room temperature for 40 min and the progress of the reaction was monitored by TLC to confirm complete consumption of the feedstock. Upon completion of the reaction, THF was removed using a rotary evaporator.The remaining aqueous phase was extracted with ethyl acetate (3 × 100 mL) and subsequently acidified with solid citric acid to pH 4. The acidified aqueous phase was again extracted with ethyl acetate (3 × 100 mL). All the ethyl acetate extracts were combined, washed with saturated brine (2×50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give the target product Boc-L-glutamic acid-1-tert-butyl ester as a colorless oil. Yield: 25 g (92% yield, calculated based on Boc-Glu(OMe)-OH). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3793 - 3797
[2] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 8730 - 8733
[3] Russian Chemical Bulletin, 2010, vol. 59, # 1, p. 110 - 115
[4] Journal of the American Chemical Society, 1993, vol. 115, # 15, p. 6646 - 6651
[5] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253

Boc-L-glutamic acid 1-tert-butyl ester(24277-39-2)Related Product Information

• Cyhalofop-butyl
• Butyl acetate
• tert-Butyl acetoacetate
• L-Glutamic acid
• BUTYL OLEATE
• Buprofezin
• tert-Butyl bromoacetate
• tert-Butyl acrylate
• Methyl acrylate
• tert-Butyl carbazate
• Tris(trimethylsilyl)phosphate
• tert-Butyl acetate
• Glutamic acid
• BOC-D-Alanine
• (BOC-AMINOOXY)ACETIC ACID
• N-Boc-L-valine
• Boc-beta-alanine
• Boc-Arg(Tos)-OH