5-Fluoro-2-nitrophenol → [3-tert-Butoxycarbonylamino-2-(5-fluoro-2-nitro-phenoxy)-propyl]-carbamic acid tert-butyl ester

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Reaction Steps

2-Nitro-5-fluorophenol (8.4 g) and (3-tert-butoxycarbonylamino-2-hydroxy-propyl)-carbamic acid tert-butyl ester (17.0 g) were dissolved in THF (60 ml) and triphenylphosphine (21 g) and di-tert-butyl-azodicarboxylate (18.4 g) were added. The exothermic reaction was cooled in an ice bath. Then the mixture was stirred at room temperature overnight. It was concentrated in vacuo and the residue was dissolved in dichloromethane, washed with water and 1M NaOH. The organic layer was dried and concentrated in vacuo. The residue was purified by chromatography (silica/dichloromethane:methanol 25:1).

Provenance & Evidence