Acetic Acid → HCID 86641124, compound

Temperature

0 °C

Compound 35.5 (46.83 g, 147.26 mmol) was dissolved in anhydrous methanol 300 mL, cooled to 0° C. and treated with 25% NaOMe in MeOH. The mixture was allowed to rise to r.t. and stirred for 8 h. The mixture was then neutralized with acetic acid and the solvent was concentrated under reduced pressure. The residue was dissolved in EtOAc, filtered and the organic layer was washed with 200 mL water. The organic layer was collected and the aqueous layer was extracted with 4×100 mL ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a column chromatography to give compound 35.6 (18.18 g, 85% yield).

1. customto rise to r.t.
2. concentrationthe solvent was concentrated under reduced pressure
3. dissolutionThe residue was dissolved in EtOAc
4. filtrationfiltered
5. washthe organic layer was washed with 200 mL water
6. customThe organic layer was collected
7. extractionthe aqueous layer was extracted with 4×100 mL ethyl acetate
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-9741cb9e32a441049cb4e1dd4e207160

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324179B2