反应详情

711 mg (16.9 mmole) of lithium hydroxide monohydrate were added, whilst ice-cooling, to a solution of 3.70 g (8.5 mmole) of (4S)-(-)-4-benzyl-N-[2(R)-benzyl-3-(morpholinocarbonyl)propionyl]-2-oxazolidinone (prepared as described in Preparation 10) in a mixture of 80 ml of tetrahydrofuran and 30 ml of water, and the mixture was then stirred at the same temperature for 3 hours. At the end of this time, the tetrahydrofuran was stripped from the reaction mixture by distillation under reduced pressure, and the residue was mixed with a 10% w/v aqueous solution of sodium hydroxide and then extracted with methylene chloride. The aqueous layer was adjusted to a pH value of 1 by the addition of concentrated hydrochloric acid, whilst ice-cooling, and was again extracted with methylene chloride. The latter methylene chloride extracts were combined, dried over anhydrous magnesium sulfate and concentrated by distillation under reduced pressure to afford 1.75 g (yield 75%) of the title compound as a white oily substance.

1. distillationAt the end of this time, the tetrahydrofuran was stripped from the reaction mixture by distillation under reduced pressure
2. additionthe residue was mixed with a 10% w/v aqueous solution of sodium hydroxide
3. extractionextracted with methylene chloride
4. additionThe aqueous layer was adjusted to a pH value of 1 by the addition of concentrated hydrochloric acid, whilst ice-
5. temperaturecooling
6. extractionwas again extracted with methylene chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated by distillation under reduced pressure