Cbz-Cyclohexyl-L-glycine Chemical Properties

Melting point:

111-114°C

Boiling point:

492.1±38.0 °C(Predicted)

Density 

1.200±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.99±0.10(Predicted)

color 

White

InChI

InChI=1/C16H21NO4/c18-15(19)14(13-9-5-2-6-10-13)17-16(20)21-11-12-7-3-1-4-8-12/h1,3-4,7-8,13-14H,2,5-6,9-11H2,(H,17,20)(H,18,19)/t14-/s3

InChIKey

CUSYTUPJAYLNFQ-WDHUHKLTNA-N

SMILES

[C@H](C1CCCCC1)(C(=O)O)NC(=O)OCC1C=CC=CC=1 |&1:0,r|

LogP

1.7 at 25℃ and pH2.5

CAS DataBase Reference

69901-75-3(CAS DataBase Reference)

Cbz-Cyclohexyl-L-glycine Usage And Synthesis

Chemical Properties

Cbz-Cyclohexyl-L-glycine is white to Off-White Solid

Uses

Cbz-Cyclohexyl-L-glycine is a gylicine derivative used in the preparation of peptides as inhibitors of serine proteases, particularly hepatitis C virus NS3-NS4A protease.

Synthesis

General Steps: Step (1): 534 mL of deionized water and 60.9 mL of 20% aqueous sodium hydroxide were added to 60.0 g of L-(+)-2-cyclohexylglycine (L-CHG) and stirred until completely dissolved. Subsequently, activated carbon was added to the solution for decolorization and supplemented with 79 mL of deionized water. Under stirring, 65.1 g of benzyl chloroformate (Cbz-Cl) and 60.9 mL of 20% aqueous sodium hydroxide solution were added slowly and dropwise to introduce a benzyloxycarbonyl (Cbz) protecting group in the L-CHG molecule. Step (2): the reaction solution obtained in step (1) (total volume 865 mL) was added to deionized water and isopropyl alcohol (IPA) in the proportions shown in Table 1, respectively. Step (3): After the completion of step (2), 4.1 mL of hydrochloric acid was added to the reaction solution to carry out the neutralization reaction, and the precipitated crystals were subsequently separated by filtration. The crystals obtained by filtration were dried to finally obtain (S)-2-(((benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid (Cbz-L-CHG). The specific results for each experimental condition are detailed in Table 1.

References

[1] Patent: US2011/152573, 2011, A1. Location in patent: Page/Page column 3

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