Z-3-CYCLOHEXYL-L-ALANINE Chemical Properties

Boiling point:

501.4±43.0 °C(Predicted)

Density 

1.167

storage temp. 

2-8°C

pka

4.00±0.10(Predicted)

Appearance

Colorless to light yellow Oil

optical activity

Consistent with structure

InChI

InChI=1/C17H23NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h2,5-6,9-10,13,15H,1,3-4,7-8,11-12H2,(H,18,21)(H,19,20)/t15-/s3

InChIKey

MNABZONTQXNLDT-UJHUVDBMNA-N

SMILES

[C@H](C(=O)O)(NC(=O)OCC1=CC=CC=C1)CC1CCCCC1 |&1:0,r|

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

Z-3-CYCLOHEXYL-L-ALANINE Usage And Synthesis

Chemical Properties

Transparent, yellow oil

Synthesis

General procedure: to a solution of (S)-2-amino-3-cyclohexylpropionic acid (10 g, 58.4 mmol) in THF/H2O (1:1, 292 ml) was added benzyl chloroformate (9.93 g, 58.4 mmol) and K2CO3 (9.67 g, 70.09 mmol). The reaction mixture was stirred at 0 °C for 0.5 h, followed by stirring at room temperature overnight. After completion of the reaction, the reaction mixture was diluted with EtOAc (200 ml) and the pH was adjusted to about 2 with 6N HCl. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated to give the solid product (S)-2-(((benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acid in 95% yield (17 g). Results of mass spectrometry analysis: MS (m/z): 306 (M + H).

References

[1] Patent: WO2006/29210, 2006, A2. Location in patent: Page/Page column 47

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