反应详情

3-(3-Fluoro-4-((3R)-3-t-butoxycarbonylamino-1-pyrrolidinyl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (5 g, 12.7 mmol), 3-hydroxyisoxazole (2.15 g, 25.3 mmol), and 1,1′-(azodicarbonyl)dipiperidine (6.39 g, 25.3 mmol) were suspended by stirring in dry tetrahydrofuran (100 ml) under nitrogen and cooled to 5° in an ice-bath. Tributylphosphine (5.12 g, 25.3 mmol) was added dropwise over 20 minutes, and the solution stirred 18 hours, allowing the temperature to rise to ambient. Reduced azo compound was filtered off, and the solution evaporated to dryness and the residue triturated with ether. The residue was purified by chromatography on a 90 g Biotage silica column, eluting with a gradient from 50 to 75% EtOAc in isohexane. Relevant fractions were combined and evaporated to give the product (3.92 g).

1. temperaturecooled to 5° in an ice-bath
2. filtrationReduced azo compound was filtered off
3. customthe solution evaporated to dryness
4. customthe residue triturated with ether
5. customThe residue was purified by chromatography on a 90 g Biotage silica column
6. washeluting with a gradient from 50 to 75% EtOAc in isohexane
7. customevaporated