Cbz-L-tert-Leucine Chemical Properties

Boiling point:

436.4±38.0 °C(Predicted)

Density 

1.160±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Oil

pka

4.01±0.10(Predicted)

color 

Pale to Light Yellow

optical activity

Consistent with structure

CAS DataBase Reference

62965-10-0

Safety Information

HazardClass 

IRRITANT

HS Code 

29225090

Cbz-L-tert-Leucine Usage And Synthesis

Chemical Properties

Pale Yellow Thick Oil

Uses

Cbz-L-tert-Leucine is a leucine derivative used in the preparation of various pharmaceutical agents such as TRPV4 antagonists, HIV-1 protease inhibitors and serine protease inhibitors.

Synthesis

Step A: Synthesis of (S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid; to a methanolic (200 mL) suspension of L-tert-leucine (11.88 g, 90.7 mmol) was sequentially added triethylamine (26.56 mL, 190 mmol) and N-(benzyloxycarbonyloxy)succinimide (24.88 g, 99.8 mmol). The reaction mixture was stirred at room temperature for 14 hours. After completion of the reaction, methanol was removed by rotary evaporator under reduced pressure to give a viscous light yellow oil. The oily substance was dissolved in ethyl acetate (100 mL) and the organic layer was washed sequentially with 1 M hydrochloric acid (15 mL) and saturated saline. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure by rotary evaporator to afford the title compound (S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid as an oil (24 g, quantitative yield).1H-NMR (CDCl3) δ: 7.43-7.36 (5H, m), 5.36 (1H, d, J = 9.4 Hz) , 5.12 (2H, br s), 4.20 (1H, d, J = 9.6 Hz), 1.02 (9H, s).LRMS: m/z 266 [M + H]+, 264 [M - H]-, 529 [2M - H]-.

References

[1] Patent: EP1210330, 2005, B1. Location in patent: Page/Page column 9-10

Cbz-L-tert-Leucine(62965-10-0)Related Product Information

• tert-Butanol
• N-Carbobenzyloxyglycine
• 6-Aminocaproic acid
• N-CARBOBENZOXY-DL-LEUCINE
• ETHANE
• Dimethyl carbonate
• Dimethyl ether
• Dimethyl sulfide
• Dimethyl sulfate
• Glycine
• L-tert-Leucine
• Dimethyl fumarate
• N,N-Dimethylformamide
• Dimethyl sulfoxide
• CBZ-L-TERT-LEUCINE DICYCLOHEXYLAMMONIUM SALT
• DL-tert-Leucine
• (R)-TERT-LEUCINOL
• Methoxycarbonyl-L-tert-leucine