N-((N-Methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine Methyl Ester → N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine

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Reaction Steps

To a solution of N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine methyl ester 10 (0.511 g, 0.00164 mol) in p-dioxane (10 mL) and H2O (5 mL) was added LiOH monohydrate (0.103 g, 0.00246 mol). After stirring at room temperature for 1 hr, the p-dioxane was removed by rotary evaporation in vacuo, and the remaining aqueous solution was treated with 1N aq HCl (2.46 mL) and extracted with ethyl acetate (4×100 mL). The combined organic extract was washed with saturated brine and dried for 15 mins over Na2SO4. Concentration in vacuo followed by CH2Cl2 chases (2x) afforded the desired compound as a white solid (0.480 g, 0.00161 mol, 98%): 1H NMR (DMSO-d6) δ 0.90 (dd, J1 =6.9 Hz, J2 =2.4 Hz, 6H), 1.24 (d, J=6.9 Hz, 6H), 1.99-2.12 (m, 1H), 2.83 (s, 3H), 2.96-3.10 (m, 1H), 3.96 (dd, J1 =8.4 Hz, J2 =6 Hz, 1H), 4.19-4.32 (m, 2H), 6.26 (d, J=8.4 Hz, 1H), 7.80 (s, 1H). Mass spectrum: (M+H)+ =298

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