Potassium ethanethioate → HCID 69543961, compound

Temperature

80 °C

To a solution of (3R)-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine (1.0 g, 3.12 mmol) (obtained as described in Reference Example 20(1)) in dimethylformamide (30 ml) was added potassium thioacetate (919 mg, 9.36 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 5.5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (3:1→1:1) as the eluant to afford (3S)-3-acetyl-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)pyrrolidine (877 mg, yield 99%) as a pale brown solid.

1. customthe completion of the reaction
2. customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
3. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-c249f17fea27447fb210dcc1dd91a506

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2