Acetohydroxamic Acid → HCID 59383899, compound

To a 250 mL three necked round-bottomed flask equipped with a mechanical stirrer under nitrogen was added anhydrous DMF (100 mL) and acetohydroxamic acid (4.65 g, 62 mmol). After a clear solution was obtained, potassium tert-butoxide (6.94 g, 62 mmol) was added. The cloudy white mixture was allowed to stir for 30 min. 2-Fluoro-3-iodo-4-methylbenzonitrile (8.0 g, 31 mmol) was added and the reaction mixture was allowed to stir at RT for 6 h. Additional acetohydroxarnic acid (1.16 g, 15.5 mmol) and potassium tert-butoxide (1.74 g, 15.5 mmol) were added, and stirring continued for 12 h. The reaction mixture was distilled under reduced pressure to remove most of the DMF and the residue was partitioned between ethyl acetate (250 mL) and sat. aqueous ammonium chloride (50 mL). The aqueous layer was washed with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, and then evaporated under reduced pressure. The crude product was loaded on an ISCO column (330 g, eluted with 20-70% ethyl acetate in hexanes) to provide the title compound as an off white crystalline solid. MS (ESI, pos. ion) m/z: 275.0 (M+1).

1. customAfter a clear solution was obtained
2. stirringto stir at RT for 6 h
3. stirringstirring
4. waitcontinued for 12 h
5. distillationThe reaction mixture was distilled under reduced pressure
6. customto remove most of the DMF
7. customthe residue was partitioned between ethyl acetate (250 mL) and sat. aqueous ammonium chloride (50 mL)
8. washThe aqueous layer was washed with ethyl acetate (2×100 mL)
9. washThe combined organic layers were washed with brine (50 mL)
10. dry with materialdried over MgSO4
11. customevaporated under reduced pressure
12. washThe crude product was loaded on an ISCO column (330 g, eluted with 20-70% ethyl acetate in hexanes)

ORD record

ord-bc3d0c2ed7964deea61b6ef3fa4833fa

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07759337B2