FMOC-VAL-OSU Chemical Properties

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

10.09±0.46(Predicted)

form 

Powder

color 

Off-white to white

optical activity

Consistent with structure

Water Solubility 

Slightly soluble in water.

Safety Information

Safety Statements 

24/25

HS Code 

29251900

FMOC-VAL-OSU Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

N-Fmoc-L-valine N-succinimidyl ester is useful for solid phase peptide synthesis techniques.

Synthesis

Dicyclohexylcarbodiimide (1.55 g, 7.52 mmol) and N-hydroxysuccinimide (762 mg, 6.63 mmol) were sequentially added to a stirred solution of Fmoc-L-valine (1.5 g, 4.42 mmol) in dichloromethane (25 mL) at room temperature. The reaction mixture was stirred continuously for 3 hours at room temperature. Upon completion of the reaction, the white solid dicyclohexylurea produced in the reaction was removed by filtration. The organic phase was washed sequentially with 0.1 N HCl solution and deionized water, followed by drying with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by fast column chromatography using 1% dichloromethane solution in methanol as eluent to give the final target product (S)-2,5-dioxopyrrolidin-1-yl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutyrate as a white solid (1.7 g, 89% yield). Mass spectrum (MS): m/z 459 [M + Na]+. 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J = 7.5 Hz, 2H), 7.68-7.55 (m, 2H), 7.43 (t, J = 7.4 Hz, 2H), 7.34 (dd, J = 15.9, 8.5 Hz, 2H), 4.70 (d, J = 4.6 Hz, 1H), 4.56-4.40 (m, 3H), 4.28 (t, J = 6.6 Hz, 1H), 2.85 (s, 4H), 2.37 (dd, J = 12.3, 6.5 Hz, 1H), 1.08 (dd, J = 11.0, 6.9 Hz, 6H).

References

[1] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 7, p. 999 - 1005
[2] Langmuir, 2010, vol. 26, # 7, p. 4990 - 4998
[3] Patent: WO2018/178060, 2018, A1. Location in patent: Page/Page column 64-66
[4] Journal of the American Chemical Society, 2015, vol. 137, # 21, p. 6932 - 6940
[5] Patent: US2017/247324, 2017, A1. Location in patent: Paragraph 0284; 0285

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