Triethylamine → (4RS,5SR)-4-(4-tert-butoxybenzyl)-5-(3-chlorophenyl)-1,3-oxazolidin-2-one

To a solution of (2RS,3RS)-2-(4-tert-butoxylbenzyl)-3-(3-chlorophenyl)-3-hydroxypropanoic acid (4.50 g, 14.3 mmol) in tetrahydrofuran (150 ml) were added diphenylphosphoryl azide (3.39 ml, 15.7 mmol) and triethylamine (3.00 ml, 21.4 mmol), and the mixture was heated under reflux for 1 hr. The reaction solution was allowed to cool and the mixture was evaporated under reduced pressure. To the residue was added water (200 ml), and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the objective substance (4.01 g, 80%).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 1 hr
3. temperatureto cool
4. customthe mixture was evaporated under reduced pressure
5. additionTo the residue was added water (200 ml)
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with water and saturated brine
8. dry with materialdried (anhydrous magnesium sulfate)
9. customevaporated under reduced pressure
10. customThe residue was recrystallized from hexane-ethyl acetate
11. customto give the objective substance (4.01 g, 80%)

ORD record

ord-58aadf9a0b6b42e88a92b32f0459a88d

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2