Z-AIB-OH Chemical Properties

Melting point:

65-69 °C(lit.)

Boiling point:

379.78°C (rough estimate)

Density 

1.215

refractive index 

1.5200 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

soluble in Methanol

form 

Powder

pka

4.09±0.10(Predicted)

color 

White

BRN 

2218009

InChI

InChI=1S/C12H15NO4/c1-12(2,10(14)15)13-11(16)17-8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3,(H,13,16)(H,14,15)

InChIKey

QKVCSJBBYNYZNM-UHFFFAOYSA-N

SMILES

C(O)(=O)[C@](C)(C)NC(OCC1=CC=CC=C1)=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

24/25-26

WGK Germany 

3

HS Code 

29242990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Z-AIB-OH Usage And Synthesis

Chemical Properties

white powder

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of Cbz-2-aminoisobutyric acid from 2-aminoisobutyric acid and benzyl chloroformate was as follows: to an aqueous solution (1 L) containing 2-aminoisobutyric acid (50 g, 0.49 mmol) and sodium carbonate (Na2CO3, 156 g, 1.47 mol), benzyl chloroformate (CbzCl, 91 g, 1.47 mmol) was slowly added over 15 min at 0 °C. 0.54 mmol) to a dioxane solution (500 mL). The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the aqueous layer was separated and retained by extraction with ether (Et2O, 2 x 500 mL). The aqueous layer was acidified with concentrated hydrochloric acid (cHCl) to pH=1 and then extracted with ethyl acetate (EtOAc, 2 × 500 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to afford a white solid Cbz-2-aminoisobutyric acid (111 g, 97% yield), which could be used for the next reaction without further purification.

References

[1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 533 - 548
[2] Patent: WO2013/114250, 2013, A1. Location in patent: Page/Page column 163
[3] Helvetica Chimica Acta, 2011, vol. 94, # 6, p. 993 - 1011
[4] Tetrahedron, 1982, vol. 38, # 14, p. 2165 - 2182
[5] Helvetica Chimica Acta, 1988, vol. 71, p. 140 - 154

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