FMOC-DAB-OH HCL Chemical Properties

Melting point:

169.5-171.7 °C

Boiling point:

593.7±50.0 °C(Predicted)

Density 

1.294±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

Powder

pka

3.52±0.10(Predicted)

color 

White to off-white

Safety Information

HazardClass 

IRRITANT

FMOC-DAB-OH HCL Usage And Synthesis

Synthesis

The general procedure for the synthesis of Fmoc-L-2,4-diaminobutyric acid (Fmoc-Dab-OH) from (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoic acid (Fmoc-Gln-OH) was as follows: A. 100 g (271.5 mmol) of Fmoc-Gln-OH was suspended in 2 L of a solvent mixture consisting of ethyl acetate, acetonitrile and water in the ratio of 2:1:1 by volume. 105.1 g (325.9 mmol) of diisopropylethylamine (DIPA) was slowly added at 20-30 °C and the reaction lasted for 72 hours. Upon completion of the reaction, 80 g of Fmoc-Dab-OH was obtained after post-processing in 86.5% yield. The product was analyzed by high performance liquid chromatography (HPLC) showing a purity of 99.6%, and its structural correctness was confirmed by infrared spectroscopy (IR) and nuclear magnetic resonance (NMR), and the relevant spectra are shown in Figures 1 and 2.

References

[1] Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 10, p. 1915 - 1924
[2] Patent: CN105348147, 2016, A. Location in patent: Paragraph 0014
[3] Synlett, 2011, # 13, p. 1917 - 1919
[4] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[5] European Journal of Medicinal Chemistry, 1995, vol. 30, # 2, p. 115 - 122

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