Potassium Hydroxide → (2E)-7-(2,3-diphenylacrylamido)-N-hydroxy heptanamide

Hydroxylamine hydrochloride (1.4 g, 19.7 mmol) in methanol (3 mL) was mixed with KOH (1.1 g, 19.7 mmol) in methanol (2.5 mL) at 0° C. and the reaction mixture was sonicated for 5 minutes. A white precipitate was formed which was filtered. The filtrate was immediately added to the methyl-(2E)-7-(2,3-diphenylacrylamido)heptanoate (0.4 g, 1.1 mmol) in dichloromethane (1 mL) and the mixture was stirred at room temperature for 30 min. Reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate, (200 mL). The organic layer was washed successively with water (3×50 mL) and brine solution (3×50 mL). The organic layer was dried over Na2SO4 and concentrated to give the crude compound, triturated with dichloromethane (20 mL), to afford the title compound as a pure colorless solid (0.230g, 58% yield). 1H NMR (DMSO-d6) δ (ppm): 1.23 (4H, m, —CH2), 1.42-1.49 (41-1, m, —CH2), 1.91-1.94 (2H, t, —CH2), 3.09-3.14 (2H, q, —CH2), 6.96-6.98 (2H, t, Ar—H), 7.15-7.17 (5H, m, Ar—H), 7.34 (1H, s, ═CH), 7.36-7.44 (4H, m, Ar—H & —NH), 9.00 (1H, s, —NH), 10.34 (1H, s, —NH). MS m/z: 367.0 (M++1). The following compounds were prepared according to the above procedure

1. customthe reaction mixture was sonicated for 5 minutes
2. customA white precipitate was formed which
3. filtrationwas filtered
4. customReaction mixture
5. extractionextracted with ethyl acetate, (200 mL)
6. washThe organic layer was washed successively with water (3×50 mL) and brine solution (3×50 mL)
7. dry with materialThe organic layer was dried over Na2SO4
8. concentrationconcentrated
9. customto give the crude compound
10. customtriturated with dichloromethane (20 mL)

ORD record

ord-25479c80f1224426bd0f900e019513a1

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476255B2