Sodium hydride → HCID 19434070, Verbindung

A solution of the product from Example 1, Step C (13.0 g, 63.3 mmol) in DMF (50 mL) was added to a suspension of sodium hydride (2.5 g of a 60% slurry in mineral oil, washed with hexane, 63.3 mmol) in DMF (300 mL) at 0° C. After stirring for 45 min, the product from Step A (10.6 g, 63.3 mmol) was added and the mixture was stirred for 18 hr, during this time the temperature slowly increased to room temperature. The reaction mixture was diluted with cold water (300 mL) and extracted with ethyl acetate (5×10 mL). The combined extracts were washed with water (3×10 mL), saturated aqueous sodium chloride (20 mL), dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, gradient, 3:1 hexane/ethyl acetate to 7:3 methylene chloride/methanol) to provide a clear oil (13.1 g, 71%) which was used in the next step.

1. washwashed with hexane, 63.3 mmol) in DMF (300 mL) at 0° C
2. stirringthe mixture was stirred for 18 hr, during this time the temperature
3. extractionextracted with ethyl acetate (5×10 mL)
4. washThe combined extracts were washed with water (3×10 mL), saturated aqueous sodium chloride (20 mL)
5. dry with materialdried (MgSO4)
6. customevaporated to a residue which
7. customwas purified by column chromatography (silica, gradient, 3:1 hexane/ethyl acetate to 7:3 methylene chloride/methanol)

ORD-Eintrag

ord-13c3309ba14e437bb6c9c1656ea435df

Quelldatensatz

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05538966