Ethyl trifluoroacetate → HCID 178471761, compound

Participants

Reaction Conditions

Reaction Steps

A 50 mL flask was charged with 6.6 mL methyl tert-butyl ether and ethyl trifluoroacetate (520 uL, 3.47 mmol). To this solution was then added 533 μL of sodium ethoxide (21% in ethanol) slowly, followed by the product of Example 26A (1.00 g, 3.47 mmol) in 3 mL of methyl tert-butyl ether over 5 minutes. After stirring overnight, the solution was quenched with sat NH4Cl and extracted with ethyl acetate (×2). The ethyl acetate layers were then evaporated to dryness, and the residue taken up in ethanol (5 mL). Two equivalents of hydrazine hydrate (35% in water) were added, and the solution heated to 70° C. overnight. After this time, the solution was cooled to room temperature and the solvent evaporated in vacuo. The residue was taken up in 1:1 methanol/DMSO and purified over RP-HPLC to afford the title product. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.03-1.15 (m, 1 H), 1.19 (t, J=7.12 Hz, 3 H), 1.37-1.60 (m, 2 H), 1.69-1.86 (m, 5 H), 2.15-2.27 (m, 2 H), 4.07 (q, J=7.12 Hz, 2 H), 6.96-7.22 (m, 1 H), 7.26-7.43 (m, 2 H), 7.63-7.80 (m, 2 H), 13.98 (s, 1H): MS (ESI) m/z 381 [M+H]+.

Provenance & Evidence