Imidazole → HCID 17819417, compound

To a well-stirred mixture of polystyryl supported triphenylphosphine (29.3 mmol) in dry dichloromethane (40 mL) under a nitrogen atmosphere was added iodine (7.44 g, 29.3 mmol). After ten minutes, imidazole (2.0 g, 29.3 mmol) was added, followed in ten minutes by a solution of N-butoxycarbonyl-3-fluorovalinol (13.3 mmol) in dichloromethane (200 mL). The mixture was heated to reflux for two hours. The cooled mixture was filtered through celite and the filtrate was evaporated. The residue was dissolved in diethyl ether (150 mL), and this solution was washed with dilute aqueous sodium thiosulfate (1×75 mL) and water (2×75 mL). The organic layer was dried (Na2SO4), filtered through a pad of silica gel and evaporated to afford 3.46 g of N-butoxycarbonyl-1-iodo-2-amino-3-fluoro-3-methyl-n-butane: 1H NMR (CDCl3) δ4.72 (br d, 1H), 3.86 (br m, 1H), 3.56 (dd, 1H), 1.47 (s, 9H), 1.43 (m, 6H) ppm.

1. additionTo a well-stirred mixture of polystyryl
2. waitAfter ten minutes
3. temperatureThe mixture was heated
4. temperatureto reflux for two hours
5. filtrationThe cooled mixture was filtered through celite
6. customthe filtrate was evaporated
7. dissolutionThe residue was dissolved in diethyl ether (150 mL)
8. washthis solution was washed with dilute aqueous sodium thiosulfate (1×75 mL) and water (2×75 mL)
9. dry with materialThe organic layer was dried (Na2SO4)
10. filtrationfiltered through a pad of silica gel
11. customevaporated

ORD record

ord-60d0239fe9854dc49686f9fe36accd8e

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05780505