3-Chloropropanesulphonyl chloride → HCID 136005954, compound

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Reaction Steps

To a 2 ml pyridine solution of 100 mg (0.280 mmol) of the compound obtained in Example 44, 85.2 μl (0.700 mmol) of 3-chloropropanesulfonyl chloride was added, and the mixture was stirred at room temperature for 8 hours. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. To the residue, 2 ml of ethanol and a 1M aqueous solution of sodium hydroxide were added, and the mixture was stirred at room temperature for 48 hours. Then, the reaction mixture was neutralized with a 1M aqueous solution of hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain 68 mg (53%) of the captioned compound.

Provenance & Evidence