BOC-D-MEVAL-OH Chemical Properties

Boiling point:

322℃

Density 

1.069

Flash point:

140℃

storage temp. 

Sealed in dry,2-8°C

form 

Solid

pka

4.03±0.10(Predicted)

color 

White to off-white

optical activity

Consistent with structure

Safety Information

HazardClass 

IRRITANT

HS Code 

2924190090

BOC-D-MEVAL-OH Usage And Synthesis

Uses

(R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylbutanoic acid is a valine derivative[1].

Synthesis

N-(tert-butoxycarbonyl)-D-valine (5 g, 11.5 mmol) was dissolved in THF (69 mL, 0.35 M) at 0 °C, followed by the addition of iodomethane (11.45 mL, 8 eq.). Under stirring, 60% NaH mineral oil dispersion (2.76 g, 3 eq.) was slowly added. The reaction mixture was stirred vigorously at room temperature overnight, after which it was diluted with ether (70 mL) and the reaction was quenched by the slow addition of water (50 mL) at 0 °C. The organic and aqueous layers were separated and the aqueous layer was extracted twice with ether (2 x 30 mL). The pH of the aqueous layer was adjusted to approximately 2 by adding saturated saline dropwise (tested using pH paper), followed by extraction with ethyl acetate (4 × 100 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuum. An oily product (4.46 g, 84% yield) was obtained, which was pure enough for the next step of the reaction. For further purification, an analytically pure sample was obtained as a white fluffy solid by fast column chromatography (silica gel, 3%-5% methanol/dichloromethane). When only 3 equivalents of iodomethane were used under similar conditions, a residue of raw material remained at the end of the reaction, probably due to competitive precipitation of the disodium salt.

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

BOC-D-MEVAL-OH(89536-85-6)Related Product Information

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