Water → 1,1-Dioxo-1,2-thiazolidine-3-carboxylic acid

To a solution of crude 2-{3-[((S)-3-chloro-phenyl)-1-dimethylaminomethyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid ethyl ester (430 mg, approx. 0.96 mmol) in tetrahydrofuran (4 mL) was added lithium hydroxide hydrate (71 mg, 1.7 mmol) followed by water (1 mL). The reaction mixture was stirred at room temperature for 2 h, and then the mixture was concentrated under reduced pressure to remove tetrahydrofuran. The remaining solution was stirred and approximately 25 drops of 1 M hydrochloric acid were added to bring the pH to 4.5. The sample was stirred for 10 min and the aqueous solution was decanted away from the yellow gum. The gum was washed with water (2 mL). The combined aqueous layers were evaporated to dryness, and dried overnight to give 2-{3-[((S)-3-chloro-phenyl)-1-dimethylaminomethyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid as a white residue (200 mg).

1. concentrationthe mixture was concentrated under reduced pressure
2. customto remove tetrahydrofuran
3. stirringThe remaining solution was stirred
4. additionapproximately 25 drops of 1 M hydrochloric acid were added
5. stirringThe sample was stirred for 10 min
6. customthe aqueous solution was decanted away from the yellow gum
7. washThe gum was washed with water (2 mL)
8. customThe combined aqueous layers were evaporated to dryness
9. customdried overnight

ORD record

ord-7b0e9db94055461e9e8a18fbe0e4c099

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314250B2