Sodium Carbonate → (S)-2-(4-Cyclohexyl-phenoxymethyl)-5-phenylsulfanylmethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

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To a solution of (S)-5-benzenesulfonylmethyl-2-(4-cyclohexyl-phenoxymethyl) -2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one (0.5 g, 1.11 mmol), prepared in accordance with the procedures described in Step 1 and 2 of Example 120, in HOAc (20 mL) was added sodium perborate tetrahydrate (0.446 g, 2.90 mmol). The reaction mixture was stirred at room temperature for 9 hours. The reaction mixture was neutralized with NaOH (2N) to pH˜7 and further to pH˜10 with Na2CO3. The mixture was extracted with EtOAc three times. The organic phase was washed with brine and dried (Na2SO4). Silica gel chromatography (2-8% methanol/CH2Cl2) provided 0.425 g of (S)-2-(4-cyclohexyl-phenoxymethyl)-5-phenylsulfanylmethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one. [α]D25 −3.80 (c 0.5, CHCl3).

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