Water → (S)-ibuprofen N-octyl-D-glucamine salt

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Initial resolution. Racemic ibuprofen (18 g, 87 mmol) was dissolved in toluene (150 mL), and water (0.5 mL) and N-octyl-D-glucamine (12.12 g, 41 mmol) were added to the solution. The mixture was heated slowly to 75° C., forming a clear solution, and the solution then cooled to 20° C. over 3 hours. The resulting precipitate was recovered by filtration, washed with toluene (50 mL), and dried to give (S)-ibuprofen N-octyl-D-glucamine salt (14.75 g, 30 mmol, MR=136.5°~137° C., [α]D =-11.2° (c=0.1, MeOH), 99% ee). The toluene liquors were saved for racemization and recycle of the contained (R)-ibuprofen.

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