Imidazole → HCID 17819417, compound

To a well-stirred mixture of polystyryl supported triphenyl phosphine (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 Celiteo® 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 grams of N-butoxycarbonyl-1-iodo-2-amino-3-fluoro-3-methyl-n-butane: 1H NMR (CDCl3) δ 4.72 (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 Celiteo®
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-cfd1d341b771461082c47311911aaac5

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763474