Toluene → HCID 131728412, compound

Participants

Reaction Conditions

Reaction Steps

N2-tert-Butyloxycarbonyl-N2-(4-fluorobenzyl)-N1-methoxy-N1-methylglycinamide oxobutanoate (1.72 g, 5.28 mmol, from Example 6, Step 4) was azeotroped with anhydrous toluene (20 mL) and dissolved in anhydrous THF (53 mL). The solution was cooled to 0° C. and treated rapidly with vinylmagnesium bromide (866 mg, 6.60 mmol) under inert atmosphere. After stirring for 20 min at 0° C. and warming to ambient temperature over 40 min, the mixture was treated with N-methylpiperazine (585 μL, 5.28 mmol) and water (8 ml) and stirred for 20 min. The reaction was partitioned between EtOAc and brine, and the organic layer was washed twice with water, dried over Na2SO4, and concentrated in vacuo. The residue was azeotroped with CHCl3 to afford the title compound as yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.26-7.17 (m, 3H), 7.03-7.00 (m, 1H), 4.45 (d, J=16.8 Hz, 2H), 3.93 (d, J=54.8 Hz, 2H), 2.67-2.45 (m, 12H), 2.27 (s, 3H), 1.46 (d, J=8.4 Hz, 9H). ES MS (M+1)=394.5.

Provenance & Evidence