Sodium Hydroxide → (S)-6-benzenesulfinyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[32-a]pyrimidin-7-one

Participants

Reaction Steps

To a solution of 2-(4-cyclohexyl-phenoxymethyl)-6-phenylsulfanyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one (0.313 g, 0.675 mmol) (prepared in accordance with the procedures set forth in Example 93), in HOAc (6 mL) was added sodium perborate tetrahydrate (0.277 g, 1.80 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then neutralized with NaOH (2N) to PH˜9. The mixture was extracted with EtOAc three times. The organic phase was washed with brine and dried (Na2SO4). Silica gel chromatography (0-6% 2-propanol/CH2Cl2) provided 0.026 g of (S)-6-benzenesulfonyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one, 0.022 g of (S)-6-benzenesulfinyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[32-a]pyrimidin-7-one (Diastereomer 1) and 0.086 g of (S)-6-benzenesulfinyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[32-a]pyrimidin-7-one (diastereomer 2).

Provenance & Evidence