2-Amino-4-(benzyloxy)benzamide → HCID 66610642, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-4-(benzyloxy)benzamide (4.0 g, 16.5 mmol) in THF (60 mL) was added a solution of 5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione (3.65 g, 18.6 mmol) from Example 16 in THF (20 mL) portionwise at rt. After heating to 63° C. for 18 h, the solution was cooled and concentrated. After addition of H2O, the solution was extracted twice with DCM. The combined organic phases were washed with brine and dried over sodium sulfate. Chromatography on silica gel eluting with 10 to 80% EtOAc/DCM afforded 4-(benzyloxy)-2-(2-(4-fluorophenyl)-2-hydroxyacetamido)benzamide as a foamy solid (4.1 g, 64%). 1H NMR (300 MHz, DMSO-d6) δ ppm 5.06 (m, 1H), 5.12 (s, 2 H) 6.68-6.74 (m, 1H) 7.14-7.20 (m, 2 H) 7.32-7.51 (m, 6 H) 7.77 (d, J=8.85 Hz, 1 H) 8.05 (br. s., 1 H) 8.30 (d, J=2.64 Hz, 1 H) 12.73 (s, 1 H). LC-MS (ESI) m/z 392 (M−2).

Provenance & Evidence