Mohammad N. Noshi
Oct 20, 2014
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Abstract
[731797-86-7] C15H22N2O2 (MW 262.3474) InChI = 1S/C15H22N2O2/c1-10(2)14(17(5)9-18)15(19)16-13-7-11(3)6-12(4)8-13/h6-10,14H,1-5H3,(H,16,19)/t14-/m0/s1 InChIKey = WWUZCRRIJZUXEZ-AWEZNQCLSA-N (the reagent is a chiral organocatalyst used in the asymmetric reduction of prochiral N-aryl ketimines with trichlorosilane) Alternate Names: (S)-N-(3,5-dimethylphenyl)-3-methyl-2-(N-methylformamido)butanamide, kenamide. Physical Data: white or yellowish white powder. Melting range: 83–86 °C;1 97–104 °C.2 Optical rotation: [α]D−19.2°, c = 1 in chloroform;1 −229°, c = 1 in chloroform.2 Solubility: sol CHCl3 (1 g mL−1) at 25 °C. Preparation: (S)-N-(3,5-dimethylphenyl)-3-methyl-2-(N-methylformamido)butanamide was synthesized efficiently from the commercially available N-Boc-L-valine via N-methylation followed by in situ mixed anhydride generation and amide formation. Removal of the Boc group followed by N-formylation via the in situ mixed anhydride afforded (S)-N-(3,5-dimethylphenyl)-3-methyl-2-(N-methylformamido)butanamide in 56% overall yield (eq 1).1 (1)