Sodium Hydroxide → (4S)-4-{[(4-Methoxyphenyl)methyl]sulfanyl}-L-proline

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Reaction Steps

4.0 g of (2S,4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine hydrochloride were dissolved in 40 ml of 2N aqueous hydrochloric acid, and the resulting solution was stirred for 1.5 hours on an oil bath at 95°-100° C. At the end of this time, the solution was cooled to room temperature, and then about 40 ml of a 2N aqueous solution of sodium hydroxide were added to the solution, whilst stirring, to adjust its pH to a value of between 4 and 6. The crystals which separated were collected by filtration, washed with water and dried in the air, to yield 3.25 g of the title compound as crystals, melting at 198°-200° C.

Provenance & Evidence