| Identification | Back Directory | [Name]
Z-AIB-OH | [CAS]
15030-72-5 | [Synonyms]
Z-AIB-OH
Cbz-Aib-OH
NSC 164086
Cbz-L-Aib-OH
Z-a-Me-Ala-OH
Z-α-methylalanine
Z-ALPHA-ME-ALA-OH
Z-2-METHYLALANINE
RARECHEM AL CF 0964
Z-ALPHA-METHYLALANINE
N-Cbz-2-Methylalanine
Z-α-aminoisobutyric acid
Z-2-AMINOISOBUTYRIC ACID
CBZ-2-AMINOISOBUTYRIC ACID
Z-ALPHA-AMINOISOBUTYRIC ACID
N-CARBOBENZYLOXY-2-METHYLALANINE
Z-Aib-OH(Z-α-aMinoisobutyric acid)
N-Cbz-2-aMino-2-Methylpropanoic acid
2-(Carbobenzoxyamino)isobutyric Acid
Z-α-aminoisobutyric acid≥ 99% (HPLC)
2-(Cbz-aMino)-2-Methylpropanoic acid
N-Carbobenzyloxy-2-methylalanine,99%
N-CARBOBENZYLOXY-2-METHYLALANINE, TECH.
N-(Benzyloxycarbonyl)-2,2-dimethylglycine
2-[(Benzyloxycarbonyl)amino]isobutyric acid
Alanine,2-methyl-N-[(phenylmethoxy)carbonyl]-
N-ALPHA-CARBOBENZOXY-ALPHA-AMINOISOBUTYRIC ACID
2-(Benzyloxycarbonylamino)-2-methylpropionic acid
2-[(Benzyloxycarbonyl)amino]-2-methylpropanoic acid | [EINECS(EC#)]
806-320-4 | [Molecular Formula]
C12H15NO4 | [MDL Number]
MFCD00004190 | [MOL File]
15030-72-5.mol | [Molecular Weight]
237.25 |
| Chemical Properties | Back Directory | [Appearance]
white powder | [Melting point ]
65-69 °C(lit.)
| [Boiling point ]
379.78°C (rough estimate) | [density ]
1.215 | [refractive index ]
1.5200 (estimate) | [storage temp. ]
-20°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 |
| Hazard Information | Back Directory | [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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