HCID 53959266, compound → HCID 19783173, compound

Participants

Reaction Steps

By the procedure of Example 1, Step G, ethyl 3-(4-bromo-2-fluorobenzyl)-2-methoxyimino-4-oxooctanoate (from Step A) was reacted with 2-chloro-5-nitrophenylhydrazine hydrochloride. The crude product was flash chromatographed twice on silica gel (first column: gradient elution with 0.5-2% MeOH in CH2Cl2 ; second column: gradient elution with 5-20% EtOAc in hexane) to give a 54% yield of the title compound as an orange oil; homogeneous by TLC in 3:1 hexane-EtOAc; mass spectrum (FAB) m/e 538, 540 (M+1)+. 400 MHz 1H NMR (CDCl3) δ0.86 (t, J=7.3 Hz, 3H), 1.02 (t, J=7.1 Hz, 3H), 1.32 (m, 2H), 1.55 (m, 2H, partially obscured by H2O peak), 2.57 (t, J=7.8 Hz, 2H), 4.10 (s, 2H, superimposed on q, J=7.2 Hz, 2H), 6.82 (dd, J≈8, 8 Hz, 1H), 7.16 (d, J≈8 Hz, 1H), 7.23 (m, 1H, partially obscured by CHCl3 peak), 7.65 (d, J=8.8 Hz, 1H), 8.25 (dd, J=8.8, 2.6 Hz, 1H), 8.33 (d, J=2.6 Hz, 1H).

Provenance & Evidence