Boc-L-Glutamic acid 5-benzylester Chemical Properties

Melting point:

69-71 °C

alpha 

-16 º (c=2, DMF)

Boiling point:

473.68°C (rough estimate)

Density 

1.1452 (rough estimate)

refractive index 

-16.5 ° (C=2, DMF)

storage temp. 

2-8°C

solubility 

Soluble in N,N- Dimethyl formamide.

pka

3.81±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

optical activity

[α]20/D 5.5±0.5°, c = 1% in acetic acid

BRN 

2226572

Sequence

Boc-Glu(OBzl)

CAS DataBase Reference

13574-13-5(CAS DataBase Reference)

EPA Substance Registry System

L-Glutamic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 5-(phenylmethyl) ester (13574-13-5)

CAS Number Unlabeled

56-86-0

CAS Number Unlabeled

13574-13-5

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29242990

MSDS

• Language:English Provider:N-(tert-Butoxycarbonyl)-L-glutamic acid 5-benzylester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Boc-L-Glutamic acid 5-benzylester Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

N-Boc-L-glutamic acid 5-benzyl ester is used as a pharmaceutical intermediate.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of Boc-L-glutamic acid-O-benzyl from L-glutamic acid-5-benzyl ester and di-tert-butyl dicarbonate is as follows: Example 28 - Preparation of Formula 125-Compound 28a-Intermediate B: (S)-5-(benzyloxy)-2-(tert-butoxycarbonyl)-5-oxopentanoic acid 1. Compound A (5.0 g, 21.1 mmol) was dissolved in a solvent mixture of dioxane and water (1:1, 40 mL) and cooled at 0°C. 2. Boc2O (5.06 g, 23.1 mmol) was added to the above solution, followed by stirring the reaction mixture at room temperature overnight. 3. After completion of the reaction, the solvent was removed by distillation under reduced pressure. 4. The residue was diluted with water (30 mL) and alkalized with Na2CO3 (0.7 g). 5. The aqueous layer was washed with EtOAc (3 x 20 mL). 6. The pH of the aqueous layer was adjusted to 2-3 with 5 M aqueous HCl followed by extraction with EtOAc (4 x 50 mL). 7. The organic extracts were combined, washed with brine and dried with Na2SO4. 8. The solvent was removed under pressure to give (S)-5-(benzyloxy)-2-(tert-butoxycarbonyl)-5-oxovaleric acid (7.1 g, 100%) as a viscous colorless oil. Product characterization: LC-MS (Agilent): retention time (Rt) 3.40 min; m/z calculated value C17H23NO6 [M + Na]+ 360.15, measured value 360.1.

References

[1] Patent: WO2012/63085, 2012, A2. Location in patent: Page/Page column 115
[2] Patent: US2013/225594, 2013, A1. Location in patent: Paragraph 0425; 0426
[3] Synthetic Communications, 1990, vol. 20, # 15, p. 2235 - 2249
[4] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 501 - 517
[5] Organic Syntheses, 1985, vol. 63, p. 160 - 160

Boc-L-Glutamic acid 5-benzylester(13574-13-5)Related Product Information

• 4-tert-Butylbenzyl chloride
• Nequinate
• tert-Butyl acetate
• Benzyl chloride
• Benzyl alcohol
• Benzyl isocyanate
• L-Glutamic acid
• tert-Butyl peroxyacetate
• CARBONYL SULFIDE
• tert-Butanol
• Folic acid
• Benzyl benzoate
• PYRAZOPHOS
• Benzyl nicotinate
• 1,1'-Carbonyldiimidazole
• Trimethoprim
• (R)-N-Boc-glutamic acid-1,5-dimethyl ester
• Boc-D-Valine