Hydrochloric Acid → 1-[(4-Methoxyphenyl)sulfonyl]-D-proline

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Reaction Steps

D-proline (15 g, 130.3 mmol) is dissolved in a 1:1 mixture of water (150 mL) and p-dioxane (150 mL) and then triethyl amine (40 mL, 287 mmol), 4-methoxyphenylsulfonyl chloride (29.0 g, 140.3 mmol), and the 4-dimethylaminopyridine (1.5 g, 13.0 mmol) are added. The solution is stirred at room temperature overnight. The reaction mixture is then treated with 1N HCl until the solution is acidic (pH=2). The resulting solution is extracted three times with ethyl acetate. The ethyl acetate layers are washed with ammonium chloride, dried (MgSO4), filtered and evaporated to give the crude compound. Cl+ MS: m/z (rel intensity) (M+ +H 286, 100 ).

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