[CH3:1][CH:2]([S:4]([NH:7][CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])(=[O:6])=[O:5])[CH3:3].[O:14]([C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1COCC1.O>[OH:13][C:9]1([C:24]2[CH:25]=[CH:26][C:21]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:22][CH:23]=2)[CH2:10][CH2:11][CH2:12][CH:8]1[NH:7][S:4]([CH:2]([CH3:1])[CH3:3])(=[O:6])=[O:5]Into a flame dried 250 mL 3 neck flask that was fitted with a thermometer and condenser, and while stirring at room temperature under a nitrogen atmosphere, 2-{[(methylethyl)sulfonyl]amino}cyclopentan-1-one (1.00 g, 4.9 mmol) in THF (40 mL) was added dropwise to 15 mL of 0.5 M 4-phenoxyphenylmagnesium bromide. The addition of 2-{[(methylethyl)sulfonyl]amino}cyclopentan-1-one was continued dropwise, keeping the temperature above 35° C. After the addition of 2-{[(methylethyl)sulfonyl]amino}cyclopentan-1-one was complete, the reaction was stirred overnight at room temperature. Enough saturated ammonium chloride in water was then added to precipitate salts and the organic layer was decanted off. The remaining salts were washed two times with ether and the combined organic layers were concentrated under reduced vacuum. The resulting semi-solid was taken into ethyl acetate, washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum to yield 2.14 g of as a dark oil. This material was purified via silica gel chromatography employing the Water's Prep. 2000 while eluting with a solvent of hexane/ethyl acetate 7:3 to provide the title compound (540 mg) as a white solid. Ion spray M.S. 374.1 (M*−1). Calculated for C20H25NO4S: Theory: C, 63.98; H, 6.71; N, 3.73. Found: C, 63.70; H, 6.77; N, 3.55.
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