Diisopropylethylamine → 3-[4-(4-Bromo-2-fluorophenyl)-1,3-thiazol-2-yl]-4,4-dimethyl-1,3-oxazolidin-2-one

Temperatur

0 °C

N,N-diisopropylethylamine (1.2 mL, 6.9 mmol) was added to a solution of 2-{[4-(4-bromo-2-fluorophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol (1.0 g, 2.9 mmol), prepared in the previous step, in 50 mL of dry methylene chloride at 0° C. Triphosgene (1.0 g, 3.4 mmol) in 10 mL of dry methylene chloride was added drop-wise over 10 min. The orange solution was stirred at 0° C. for 3 h and then allowed to warm to room temperature. The reaction was washed with 2N HCl and the aqueous layer was extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 1.2 g of a green residue. The crude product was purified on silica gel using a step-wise gradient of 5-30% ethyl acetate:hexane to give the title compound (0.9 g, 89%). MS (ES) m/z 372 [M+H]+.

1. temperatureto warm to room temperature
2. washThe reaction was washed with 2N HCl
3. extractionthe aqueous layer was extracted with methylene chloride
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-0829dade7810414c9f7d08dd69b4f279

Quelldatensatz

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07618990B2