Hydrazine hydrate (1:1) → (S)-5-(aminomethyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one

A solution of phthalimide 95 (23.3 g, 50.0 mmol) in ethanol (EtOH, 150 mL) was treated with hydrazine monohydrate (12.52 g, 12.1 mL, 250 mmol, 5.0 equiv) at 25° C., and the resulting reaction mixture was warmed to reflux for 2 h. A white precipitate formed as the reaction mixture refluxed. When TLC and HPLC showed that the reaction was complete, the reaction mixture was cooled to room temperature before being quenched with H2O (100 mL). The aqueous solution was then extracted with CH2Cl2 (3×200 mL), and the combined organic extracts were washed with H2O (2×100 mL) and saturated aqueous NaCl (100 mL), dried over MgSO4, and concentrated in vacuo. The residue was further dried in vacuo to afford the desired (5S)-5-aminomethyl-3-(3-fluoro-4-iodo-phenyl)-oxazolidin-2-one (amine 96, 16.0 g, 95.2% yield) as a white powder. This product was directly used in the subsequent reactions without further purification. C10H10FIN2O2, LCMS (EI) m/e 337 (M++H).

1. customthe resulting reaction mixture
2. temperaturewas warmed
3. temperatureto reflux for 2 h
4. customA white precipitate formed as the reaction mixture
5. temperaturerefluxed
6. custombefore being quenched with H2O (100 mL)
7. extractionThe aqueous solution was then extracted with CH2Cl2 (3×200 mL)
8. washthe combined organic extracts were washed with H2O (2×100 mL) and saturated aqueous NaCl (100 mL)
9. dry with materialdried over MgSO4
10. concentrationconcentrated in vacuo
11. customThe residue was further dried in vacuo

ORD record

ord-434f2ef8003141b4b9033423c0cf5ab1

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129259B2