Lithium hydroxide, monohydrate → [(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid

The compound (1.5 g, 3.83 mmol) prepared in Example 26 was dissolved in tetrahydrofuran (100 ml) and methanol (50 ml). Lithium hydroxide monohydrate (640 mg, 15.3 mmol) was dissolved in water (50 ml) and added to the reaction solution, which was then stirred for 4 h at room temperature. After completion of the reaction, the reaction solution was distilled under reduced pressure to remove tetrahydrofuran and methanol. 1N hydrochloric acid solution was added to the residue, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure and separated by column chromatography to give the title compound (13.1 g, Yield 92%).

1. additionadded to the reaction solution, which
2. customAfter completion of the reaction
3. distillationthe reaction solution was distilled under reduced pressure
4. customto remove tetrahydrofuran and methanol
5. addition1N hydrochloric acid solution was added to the residue
6. extractionthe mixture was extracted with ethyl acetate
7. washwashed with saturated sodium chloride solution
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. distillationThe filtrate was distilled under reduced pressure
11. customseparated by column chromatography

ORD record

ord-b18d7095108d4e77b1d4f2b8d535ab43

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309586B2