Sodium Hydroxide → HCID 15410800, compound

To a cooled solution (5° C.) of dibenzyl 2-[(benzylsulfanyl)methyl]pentanedioate (15.2 g, 33.9 mmol) in tetrahydrofuran (750 mL) was added 0.1 N NaOH (745 mL, 74.5 mmol NaOH) with stirring. The cloudy reaction mixture was allowed to warm to room temperature. After 16 hours, the reaction mixture had become homogenous. The solution was concentrated under reduced pressure to remove the tetrahydrofuran. The remaining aqueous solution was washed with ethyl acetate, then made acidic (pH 1) with concentrated HCl. The mixture was extracted twice with ethyl acetate. The ethyl acetate was removed under reduced pressure and the resulting waxy solid was purified by column chromatography to yield 6.9 g (76%) of white solid.

1. customThe cloudy reaction mixture
2. concentrationThe solution was concentrated under reduced pressure
3. customto remove the tetrahydrofuran
4. washThe remaining aqueous solution was washed with ethyl acetate
5. extractionThe mixture was extracted twice with ethyl acetate
6. customThe ethyl acetate was removed under reduced pressure
7. customthe resulting waxy solid was purified by column chromatography

ORD record

ord-ebfec23b076f48afb0a7cfa44a5a367a

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06395718B1