Boc-N-Me-Val-OH

Chemical properties

White powder

The Uses of Boc-N-Me-Val-OH

N-Boc-N-methyl-L-valine is an amino acid derived compound that functions as a useful pharmaceutical intermediate and also employed as a reagent used in organic synthesis. It is used in the synthesis of lactam analog of actinomycin D, a potential antitumor chemotherapeutic agent.

Synthesis

To a solution of N-BOC-valine 1 (217 mg, 1 mmol) and iodomethane(1.42 g, 10 mmol) in anhydrous tetrahydrofuran (THF,20 mL) was added neat sodium hydride (240 mg, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. The mixture was then quenched with water (30 mL). The reaction mixture was extracted with ethyl acetate (EtOAc, 2 15 mL) and the aqueous solution was acidified to pH 3, after which it was extracted with EtOAc (3 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and evaporated to afford the corresponding Boc-N-Me-Val-OH (thick colorless oil), 99% yield.

References

[1] Masashi Shiotsuki. “Molecular weight dependence of helical conformation of amino acid-based polyphenylacetylenes.” Journal of Polymer Science Part A: Polymer Chemistry 49 22 (2011): 4921–4925.