Sodium Hydroxide → 2307752-00-5

To a solution of Intermediate 238B (200 mg, 1.218 mmol) in THF (1 mL), MeOH (0.3 mL) and water (1 mL) was added NaOH (97 mg, 2.437 mmol) and the resulting solution was stirred at RT for 12 h. The volatiles were removed under reduced pressure and the residue was added water and extracted with ethyl acetate. The pH of the aqueous layer was adjusted to 4 using an aqueous solution of 1.5 N HCl and the compounds were extracted with EtOAc (3×10 mL). The combined organic layer was dried on Na2SO4, filtered and filtrate evaporated under reduced pressure to afford Intermediate 238C as a viscous liquid (120 mg, 65.6% yield). The crude product was taken further without any purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.24 (bs, 1H), 5.87-6.21 (m, 1H), 3.03 (q, J=8.85 Hz, 1H), 2.89 (dd, J=8.82, 4.05 Hz, 1H) 1.94-2.14 (m, 2H) 1.79-1.94 (m, 2H).

1. customThe volatiles were removed under reduced pressure
2. additionthe residue was added water
3. extractionextracted with ethyl acetate
4. extractionthe compounds were extracted with EtOAc (3×10 mL)
5. customThe combined organic layer was dried on Na2SO4
6. filtrationfiltered
7. customfiltrate evaporated under reduced pressure

ORD record

ord-191143ae37214b9cbf2b344d63887117

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273058B2