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

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Racemic ibuprofen (18.03 g, 87.4 mmol), N-methyl-D-glucamine (8.2 g, 42 mmol), water (0.5 mL), and toluene (150 mL) were heated to 50° C., forming a clear solution. The solution was cooled to 20° C., then in an ice bath, and allowed to stand for 48 hours. The resulting crystalline precipitate was recovered by filtration at 20° C., washed with toluene (30 mL), and dried to give (S)-ibuprofen N-methyl-D-glucamine salt (11.9 g, 68% yield, 92% ee).

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