Fmoc-cycloleucine Chemical Properties

Melting point:

187 °C(dec.)

Boiling point:

579.4±29.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

soluble in Dimethylformamide

form 

powder to crystal

pka

4.08±0.20(Predicted)

color 

White to Light yellow

BRN 

5995036

CAS DataBase Reference

117322-30-2(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

Fmoc-cycloleucine Usage And Synthesis

Chemical Properties

White powder

Uses

Fmoc-cycloleucine is a reagent in the development of selective inhibitors of nuclear hormone receptors.

Synthesis

General procedure for the synthesis of Fmoc-cycloleucine from 9-fluorenylmethyl-N-succinimidyl carbonate (Fmoc-OSu) and 1-aminocyclopentanecarboxylic acid: Fmoc-OSu (3.13 g, 9.3 mmol) was added to a mixture of acetonitrile/water (100 mL) and sodium bicarbonate (NaHCO3, 1.63 g, 1.4 mmol) containing 1-aminocyclopentanecarboxylic acid (1.0 g, 7.8 mmol) and sodium bicarbonate (NaHCO3, 1.63 g, 1.4 mmol). 19.4 mmol) in a mixed acetonitrile/water (100 mL, 1:1 v/v) solution. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, most of the solvent was removed by distillation under reduced pressure. Subsequently, the pH of the reaction mixture was adjusted to 2 with 2N hydrochloric acid (HCl) and extracted with dichloromethane (DCM). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4) and then concentrated. Finally, the residue was purified by silica gel fast column chromatography (petroleum ether/ethyl acetate=20:1) to afford the target product 1 -(((9H-fluoren-9-yl)methoxy)carbonylamino)cyclopentanecarboxylic acid (Compound 4 of Example A, 0.75 g, 28% yield) as a white solid.

References

[1] Journal of the American Chemical Society, 2000, vol. 122, # 37, p. 8898 - 8909
[2] Patent: WO2012/119941, 2012, A1. Location in patent: Page/Page column 110
[3] Journal of the American Chemical Society, 2003, vol. 125, # 23, p. 6852 - 6853
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 18, p. 5694 - 5706

Fmoc-cycloleucine(117322-30-2)Related Product Information

• DABSYL-L-METHIONINE
• Cyclopentane
• FMOC-D-NLE-OH
• 1-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-HYDROXY-CYCLOPENTANECARBOXYLIC ACID
• Cycloleucine
• 3-TERT-BUTOXY-1-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-CYCLOPENTANECARBOXYLIC ACID
• Fmoc-cycloleucine
• ETHYL N-FMOC-AMINO-(3-HYDROXY-CYCLOPENTYL)CARBOXYLATE
• Fmoc-Aib-OH