Sodium Hydroxide → (S)-2-((((2,2-Dimethylhex-5-en-1-yl)oxy)carbonyl)amino)-3,3-dimethylbutanoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,2-dimethylhex-5-en-1-ol (10.75 g, 83.85 mmol) in anhydrous 1,4-dioxane (100 mL), at 0° C. and under nitrogen, was added triphosgene (13.69 g, 46.12 mmol) and then DIPEA (14.61 mL, 83.85 mmol) cautiously. This reaction solution was stirred at 22° C. for 1 hour, cooled to 0° C. and added slowly 1N NaOH (83.85 mL, 83.85 mmol) and L-tert-leucine (11.00 g, 83.85 mmol), then stirred at 22° C. for 20 hours. The reaction solution was basified to pH 10 with 1N NaOH, washed with CH2Cl2 (3×100 mL), acidified to pH 5 with 1N HCl and extracted with CH2Cl2 (3×150 mL). The combined CH2Cl2 layer was washed with water (100 mL), dried over Na2SO4, filtered and concentrated to give the title product (20.26 g, 84.66%). 1H NMR (500 MHz, CDCl3) δ 5.85-5.77 (m, 1H); 5.24 (d, 1H); 5.01 (d, 1H); 4.93 (d, 1H); 4.20 (d, 1H); 3.86 (d, 1H); 3.79 (d, 1H); 2.01 (m, 2H); 1.36 (m, 2 H); 1.04 (s, 9H); 0.92 (m, 6H) ppm. LRMS (ESI) m/z 286 [(M+H)+; calcd for C15H28NO4: 286].

Provenance & Evidence