1H-Benzo[d]imidazole-2-sulfonyl chloride → 1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarboxylic acid

참여 물질

반응 단계

(2S)-2-Piperidinecarboxylic acid L-tartrate (42 g) [see Preparation 1] was dissolved in 10% w/w aqueous sodium hydroxide solution (600 ml) and 1H-benzo[d]imidazole-2-sulfonyl chloride (39 g) [see Preparation 8] was added. The reaction mixture was stirred at room temperature for 56 hours after which time the product was extracted with ethyl acetate. The organic layer was separated, 2N aqueous hydrochloric acid solution added and the acidic aqueous layer extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with 95:5:0.5, by volume, dichloromethane:methanol:glacial acetic acid to afford 1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarboxylic acid (17.5 g).

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