Sodium hydride → tert-Butyl 4-{1-[2-(5-bromo-2,3-difluorophenyl)-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate

To a suspension of NaH (60 wt % in mineral oil, 0.129 g, 3.23 mmol) in DMF (5 mL) at 0° C. was add a solution of the product from Step D (0.900 g, 2.15 mmol) in DMF (2 mL). The suspension was stirred for 30 minutes, then a solution of tert-butyl 4-(1-bromobutyl)benzoate (0.742 g, 2.37 mmol) in DMF (2 mL) was added. The mixture was stirred at 0° C. for two hours then diluted with saturated NaCl (aq, 50 mL), then the product was extracted with EtOAc (3×30 mL). The combined organic extracts were washed with water then saturated NaCl (aq), dried over MgSO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-50% toluene/hexanes to afford racemic mixtures of both diastereomers of the title compound.

1. stirringThe mixture was stirred at 0° C. for two hours
2. extractionthe product was extracted with EtOAc (3×30 mL)
3. washThe combined organic extracts were washed with water
4. dry with materialsaturated NaCl (aq), dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting residue was purified by silica gel chromatography
8. washeluting with 0-50% toluene/hexanes

ORDレコード

ord-2c68047ae8144e36ab75a82c423a18e3

出典データセット

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08318667B2