Hydrochloric Acid → HCID 69595574, compound

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Reaction Steps

Toluene-4-thiosulfonic acid S-(4-tert-butoxycarbonylamino-2-tert-butyl-5-methylphenyl) ester (33a) (70.0 grams, 156 mmol) was dissolved in ethyl ether (500 mL). Anhydrous hydrogen chloride gas was bubbled through the solution while maintaining the temperature between 12 and 17° C. A precipitate formed after about 1 hour. The hydrogen chloride gas treatment was continued for an additional 3 hours at 17-25° C. The resulting mixture was allowed to stir overnight at room temperature and filtered and the product washed with ethyl ether (1.2) and vacuum dried at 40° C. to give 59 g (0.15 mmol, 96% yield) toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methylphenyl) ester hydrochloride (29b): mp: 169° C. (dec); Assay (HPLC): 99.8 area %.

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