Phosphate → N-Cyclohexyl-N'-[3-({2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]ethoxy}methyl)phenyl]urea

Temperature

65 °C

Potassium trimethylsilanolate (0.177 g) was added to a solution of N-cyclohexyl-N′-(3-{[2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl}phenyl)urea (0.207 g) in deoxygenated anhydrous THF (6 ml) whilst stirring under nitrogen. The reaction mixture was heated to 65° C. for 4.5 h, at which point the reaction mixture was cooled to room temperature. Phosphate buffer (25 ml, pH6.5) was added and the mixture left to stir for 10 min before extracting with EtOAc (3×25 ml). The combined organic layers were separated and dried over Na2SO4 before filtering. Solvent evaporation in vacuo gave a residue which was purified by Biotage. Elution with 150:8:1 dichloromethane:EtOH:ammonia followed by solvent evaporation in vacuo gave the title compound (0.138 g). LCMS RT=2.87 min, ES+ve 598 (MH)+.

1. temperaturewas cooled to room temperature
2. waitthe mixture left
3. stirringto stir for 10 min
4. extractionbefore extracting with EtOAc (3×25 ml)
5. customThe combined organic layers were separated
6. dry with materialdried over Na2SO4
7. filtrationbefore filtering
8. customSolvent evaporation in vacuo
9. customgave a residue which
10. customwas purified by Biotage
11. washElution with 150:8:1 dichloromethane
12. customEtOH:ammonia followed by solvent evaporation in vacuo

ORD record

ord-b3ad2e0b4b004241a9fcc9fdc876d90e

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361787B2