1-Propanesulfonyl chloride → HCID 66702030, compound

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Reaction Steps

Propane-1-sulfonyl chloride (0.14 g) in DCM (1 ml) was added to a solution of the subtitle product of Example 3 step (0.2 g) in DCM (3 ml) and N,N-diisopropylethylamine (0.14 g) at 0° C. The reaction mixture was stirred for 24 h at room temperature. To the reaction mixture more N,N-diisopropylethylamine (0.14 g) was added and the reaction mixture was stirred for an additional 24 h. The DCM was removed under reduced pressure and the residue dissolved in THF (2 ml). To this mixture sodium hydroxide (10%, 2 ml) was added and stirred overnight. The reaction mixture was diluted with EtOAc (50 ml). The organic layer was separated from the aqueous layer and evaporated to dryness. To the residue was added aqueous hydrochloric acid (1M, 30 ml) and THF (10 ml). This was stirred at room temperature for 3 h. The mixture was extracted with EtOAc (2×50 ml). The organics were washed with brine (30 ml). The combined organic layers were dried (MgSO4) and concentrated. This material was purified by reverse phase HPLC (90% to 5% 0.02M ammonium hydroxide/acetonitrile) to yield the title compound as a white solid. Yield: 30 mg.

Provenance & Evidence