Methanol → HCID 42613072, compound

Temperature

65 °C

A 5M aqueous solution of potassium hydroxide (5 mL) was added to a stirred solution of the product from step (vi) (0.59 g) in MeOH (10 mL). The mixture was stirred at 65° C. for 15 h and allowed to cool. The organic solvent was removed under reduced pressure and the aqueous phase acidified to pH 7 with concentrated HCl. The aqueous phase was extracted with EtOAc and the combined organic phase dried and evaporated under reduced pressure. The residue was dissolved in MeOH (10 mL) and concentrated sulfuric acid (5 mL) added. The mixture was heated at 70° C. for 2 h and allowed to cool. The mixture was poured into saturated aqueous NaHCO3 (30 mL) and the aqueous phase extracted with EtOAc. The combined organic phase was dried and evaporated under reduced pressure. The residue was purified by chromotography eluting with 5% MeOH in DCM to give the title compound 0.24 g.

1. temperatureto cool
2. customThe organic solvent was removed under reduced pressure
3. extractionThe aqueous phase was extracted with EtOAc
4. customthe combined organic phase dried
5. customevaporated under reduced pressure
6. dissolutionThe residue was dissolved in MeOH (10 mL)
7. additionconcentrated sulfuric acid (5 mL) added
8. temperatureThe mixture was heated at 70° C. for 2 h
9. temperatureto cool
10. additionThe mixture was poured into saturated aqueous NaHCO3 (30 mL)
11. extractionthe aqueous phase extracted with EtOAc
12. customThe combined organic phase was dried
13. customevaporated under reduced pressure
14. customThe residue was purified by chromotography
15. washeluting with 5% MeOH in DCM

ORD record

ord-0c9f0d36eb8046fda3c3816a944f5689

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268990B2