FMOC-L-2-FURYLALANINE

FMOC-L-2-FURYLALANINE Property

Melting point:

129.7 °C

Boiling point:

505.72°C (rough estimate)

Density 

1.318

refractive index 

1.5614 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

3.62±0.10(Predicted)

form 

Solid

color 

White to Off-White

CAS DataBase Reference

159611-02-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2932190090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

FMOC-L-2-FURYLALANINE Chemical Properties,Usage,Production

Chemical Properties

white to off-white powder

Uses

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(furan-2-yl)propanoic acid is an alanine derivative[1].

Synthesis

Methyl (S)-2-amino-3-(furan-2-yl)propanoate (1 g, 6.5 mmol) was dissolved in toluene as the starting material. 2M LiOH aqueous solution (3.27 ml, 6.5 mmol) and dioxane (3.27 ml) were slowly added to the reaction system at 0 °C under nitrogen protection and the reaction mixture was stirred at room temperature overnight. The progress of the reaction was monitored by TLC (Spreader: CHCl3/MeOH/NH3 aqueous solution = 1/1/0.1) to confirm complete hydrolysis of the ester group. Subsequently, 1M aqueous NaHCO3 (9.75 ml, 9.75 mmol) dissolved in dioxane (10 ml) and methyl 9-fluorenyl chloroformate (2.5 g, 9.75 mmol) were added to the reaction solution and stirring was continued for 1 hour. After completion of the reaction, the dioxane was removed by distillation under reduced pressure and the remaining aqueous phase was acidified with 10% KHSO4 solution to pH=2. The aqueous phase was extracted with CHCl3 (3×20 ml), the organic phases were combined and dried over anhydrous MgSO4. After concentration under reduced pressure, the target product (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(furan-2-yl)propanoic acid (1.3 g, 53% yield) was purified by fast column chromatography (eluent: hexane/ethyl acetate/acetic acid=10/10/1) as white crystals. The product was characterized by 1H NMR and 13C NMR and the data were consistent with the expected structure.

References

[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144. DOI:10.1080/10408398.2012.708368