Hydrochloric Acid → HCID 67463924, compound

A solution of 4 N hydrochloric acid in ethyl acetate (18 mL) was added to tert-butyl {(R)-1-(tert-butyldiphenylsilanyloxymethyl)-2-[2-(4-chlorophenyl)-2-oxoethoxy]ethyl}carbamate (960 mg) under ice-cooling. The reaction solution was stirred under ice-cooling for 30 minutes and subsequently at room temperature for 30 minutes, and then concentrated under reduced pressure. Platinum oxide (37.4 mg) was added to a solution of the resulting residue in methanol (18 mL), and the reaction solution was stirred in a hydrogen atmosphere at room temperature for one hour. The reaction solution was filtered through celite. A saturated sodium bicarbonate solution and ethyl acetate were added to the filtrate, and the organic layer was separated. The organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent solvent: heptane-ethyl acetate system) to obtain a crude product. A 1 M solution of tetrabutylammonium fluoride in THF (0.947 mL) was added to a solution of the resulting crude product in THF (5 mL), and the reaction solution was stirred at room temperature for one hour. A saturated ammonium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent solvent: heptane-ethyl acetate system) to obtain 86 mg of the title compound. The property values of the compound are as follows.

1. temperaturecooling
2. concentrationconcentrated under reduced pressure
3. additionPlatinum oxide (37.4 mg) was added to a solution of the resulting residue in methanol (18 mL)
4. stirringthe reaction solution was stirred in a hydrogen atmosphere at room temperature for one hour
5. filtrationThe reaction solution was filtered through celite
6. additionA saturated sodium bicarbonate solution and ethyl acetate were added to the filtrate
7. customthe organic layer was separated
8. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine
9. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (eluent solvent: heptane-ethyl acetate system)
12. customto obtain a crude product
13. stirringthe reaction solution was stirred at room temperature for one hour
14. customthe organic layer was separated
15. washThe resulting organic layer was washed with brine
16. dry with materialdried over anhydrous magnesium sulfate
17. concentrationconcentrated under reduced pressure
18. customThe residue was purified by silica gel column chromatography (eluent solvent: heptane-ethyl acetate system)

ORD record

ord-4da85144b68643dfbf279241fbe92519

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048878B2