BOC-LYS-OTBU Chemical Properties

Boiling point:

406.7±40.0 °C(Predicted)

Density 

1.021±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform (Sparingly), Methanol (Sparingly)

pka

11.16±0.46(Predicted)

form 

Solid

color 

Off-White

optical activity

7.867°(C=0.01g/ml CHCL3)

InChI

InChI=1S/C15H30N2O4/c1-14(2,3)20-12(18)11(9-7-8-10-16)17-13(19)21-15(4,5)6/h11H,7-10,16H2,1-6H3,(H,17,19)/t11-/m0/s1

InChIKey

LVUBESNUUMLEHL-NSHDSACASA-N

SMILES

C(OC(C)(C)C)(=O)[C@H](CCCCN)NC(OC(C)(C)C)=O

BOC-LYS-OTBU Usage And Synthesis

Uses

N-Boc-Lysine Tert-butyl Ester is used in preparation of Tetrahydroisoquinoline derivatives as blood coagulation factor inhibitors useful in the treatment of thromboembolic disorders.

Synthesis

General procedure for the synthesis of (S)-6-amino-2-((tert-butoxycarbonyl)amino)hexanoic acid tert-butyl ester from (S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)hexanoic acid tert-butyl ester: (0133) (0134) (S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)hexanoic acid tert-butyl ester was butyl ester (98.8 mg, 0.226 mmol) and 10% Pd/C (12.1 mg, 11.4 μmol) were dissolved in methanol (1 mL) and stirred for 2 h at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the solid catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated under reduced pressure to afford tert-butyl (S)-6-amino-2-((tert-butoxycarbonyl)amino)hexanoate in 96% (66.1 mg) yield. The resulting product was used directly in the next reaction without further purification.

References

[1] Angewandte Chemie - International Edition, 2009, vol. 48, # 9, p. 1633 - 1635
[2] Patent: EP2952504, 2015, A1. Location in patent: Paragraph 0133-0134
[3] Tetrahedron Letters, 2014, vol. 55, # 46, p. 6343 - 6346
[4] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 15, p. 3957 - 3965
[5] Journal of the American Chemical Society, 1997, vol. 119, # 17, p. 4086 - 4087