Selectfluor → HCID 68902495, compound

The Selectfluor® reagent (2.2125 g, 6.25 mmol) in 250 mL of acetonitrile was added under nitrogen dropwise over 1.5 h to a solution of (4S)-3-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-4-ethyl-1,3-oxazolidin-2-one (2.0015 g, 5.67 mmol), prepared in step 2 of Example 7, in 250 mL of acetonitrile at room temperature. After the addition, the reaction was stirred at room temperature for 21.5 h. The reaction was concentrated under reduced pressure to remove the acetonitrile. The residue was partitioned between methylene chloride and 2 N HCl. The organic layer was separated and the aqueous layer extracted three times with methylene chloride. The combined extracts were dried (anhydrous MgSO4), filtered and the solvent removed under reduced pressure to give 2.11 g of a tan foam. Purification of the foam on 800 g of silica gel (230-400 mesh) using 50% methylene chloride-hexane to 100% methylene chloride as the eluents gave the title compound (914.8 mg, 44%) as a white solid, mp 105-107° C.; MS (ES) m/z 370.9 [M+H]+; Anal. Calcd for C14H12BrFN2O2S: C, 45.30; H, 3.26; N, 7.55. Found: C, 45.53; H, 3.09; N, 7.37.

1. additionAfter the addition
2. concentrationThe reaction was concentrated under reduced pressure
3. customto remove the acetonitrile
4. customThe residue was partitioned between methylene chloride and 2 N HCl
5. customThe organic layer was separated
6. extractionthe aqueous layer extracted three times with methylene chloride
7. dry with materialThe combined extracts were dried (anhydrous MgSO4)
8. filtrationfiltered
9. customthe solvent removed under reduced pressure

ORD record

ord-dee9676b32d246ea9dbe87700f066e75

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07618990B2