L-GLUTAMIC BENZYL ESTER

L-GLUTAMIC BENZYL ESTER Property

Boiling point:

153-155 °C(Press: 0.05 Torr)

Density 

1.1645 g/cm3

storage temp. 

Sealed in dry,Room Temperature

pka

4.61±0.10(Predicted)

Appearance

Colorless to light yellow Solid-liquid mixture

InChI

InChI=1S/C12H14O4/c13-11(14)7-4-8-12(15)16-9-10-5-2-1-3-6-10/h1-3,5-6H,4,7-9H2,(H,13,14)

InChIKey

WRSDJJXJDSEUSQ-UHFFFAOYSA-N

SMILES

C(OCC1=CC=CC=C1)(=O)CCCC(O)=O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

L-GLUTAMIC BENZYL ESTER Chemical Properties,Usage,Production

Uses

1-(Phenylmethyl) Ester Pentanedioic Acid is a useful reagent for organic synthesis.

Synthesis

GENERAL METHOD: To a solution of glutaric anhydride (1.0 g, 10 mmol) in DMF (4 mL) was slowly added benzyl alcohol (0.94 mL, 9.09 mmol) and N,N-diisopropylethylamine (DIEA, 1.93 mL, 11 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed using a rotary evaporator (Speed-vac). The residue was dissolved in ethyl acetate (50 mL) and washed sequentially with saturated sodium chloride solution (10 mL x 2). The organic phase was separated and extracted with aqueous sodium bicarbonate solution (5M, 5mL x 3). The aqueous phase extracts were combined and the pH was adjusted to 4 with aqueous citric acid (5M) and extracted with ethyl acetate (30mL × 3). All ethyl acetate extracts were combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 1,5-glutaric acid monobenzoate as a white solid (1.66 g, 89% yield).

References

[1] Chemical Biology and Drug Design, 2018, vol. 92, # 2, p. 1403 - 1408
[2] Synthetic Communications, 2001, vol. 31, # 9, p. 1399 - 1419
[3] Journal of the American Chemical Society, 1996, vol. 118, # 29, p. 6826 - 6840
[4] Chemical Communications, 2011, vol. 47, # 17, p. 4896 - 4898
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 23, p. 7507 - 7514