CBZ-1-AMINO-1-CYCLOPENTANECARBOXYLIC ACID Chemical Properties

Melting point:

95-98 °C

Boiling point:

468.2±34.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.12±0.20(Predicted)

Safety Information

HS Code 

2917399590

CBZ-1-AMINO-1-CYCLOPENTANECARBOXYLIC ACID Usage And Synthesis

Synthesis

To a 1:1 dioxane/water (60 mL) solution of 1-aminocyclopentanecarboxylic acid (3.0 g, 23.2 mmol) was slowly added sodium carbonate (Na2CO3, 12.3 g, 116 mmol), followed by dropwise addition of benzyl chloroformate (3.6 mL, 25.5 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the pH was carefully adjusted to 2 with 1 M hydrochloric acid (HCl) and then extracted with ethyl acetate (EtOAc, 3 × 30 mL). The organic phases were combined, washed with saturated saline (30 mL), dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give a light yellow oily crude product. The crude product was analyzed by LCMS and NMR as a mixture of Cbz-cycloleucine and its corresponding benzyl ester. The crude product was dissolved in 1:1 tetrahydrofuran/water (THF/H2O, 60 mL) and lithium hydroxide (LiOH, 2.67 g, 116 mmol) was added. The mixture was stirred overnight at room temperature and then washed with ether (Et2O, 3 × 30 mL), then acidified with 1 M HCl to pH = 2 and finally extracted with EtOAc (3 × 30 mL). The organic phases were combined, washed with saturated saline (30 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give Cbz-cycloleucine (4.76 g, 78% yield).LCMS: m/z 264 [M + H]+.

References

[1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 238 - 244
[2] Patent: US2010/317865, 2010, A1. Location in patent: Page/Page column 14; 15
[3] Patent: WO2009/106844, 2009, A1. Location in patent: Page/Page column 39
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2001, vol. 40, # 1, p. 70 - 74
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 533 - 548

CBZ-1-AMINO-1-CYCLOPENTANECARBOXYLIC ACID(17191-44-5)Related Product Information

• 1-(Cbz-amino)cyclopropanecarboxylic acid
• Cyclopentanecarboxylic acid
• Z-D-NLE-OH
• Cycloleucine
• Z-AIB-OH
• CBZ-1-AMINO-1-CYCLOPENTANECARBOXYLIC ACID