Water → HCID 59735302, compound

To a solution containing the oxazolidinone (5.0 g, 13.9 mmol) in dry THF (50 mL) was added potassium-t-butoxide (2.03 g, 18.1 mmol, 1.3 equiv) at RT and stirred under N2 atm for 0.5 h. To this solution was added ethyl iodide (3.25 g, 20.8 mmol, 1.5 equiv) and stirred for 2 h after which TLC (1:1 hex-EtOAc) showed completion of reaction. The reaction was quenched by adding satd. NH4Cl solution. THF was removed on rotovap and residue diluted with CH2Cl2 (100 mL). Organic layer washed with brine and dried (MgSO4). Removal of solvent gave a light yellow oil. This crude product was taken in CH2Cl2 (50 mL). Added trifluoroacetic acid (4.75 g, 41.7 mmol, 3.0 equiv)-water (1.0 g, 55.5 mmol, 4 equiv) dropwise and stirred for 2 h. The solvent was removed on rotovap and residue purified by flash column chromatography (silica gel, EtOAc) to get the product as a colorless oil (1.3 g, 66% in two steps).

1. customcompletion of reaction
2. customThe reaction was quenched
3. additionby adding satd
4. customTHF was removed on rotovap and residue
5. additiondiluted with CH2Cl2 (100 mL)
6. washOrganic layer washed with brine
7. dry with materialdried (MgSO4)
8. customRemoval of solvent
9. customgave a light yellow oil
10. customThe solvent was removed on rotovap and residue
11. custompurified by flash column chromatography (silica gel, EtOAc)

ORD record

ord-f91bab0e5ce442f8be062c492383b636

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07390825B1