Sodium Hydroxide → HCID 118062043, compound

A solution of Intermediate 258D (0.07 g, 0.364 mmol) and NaOH (0.036 g, 0.910 mmol) in THF (2 mL) and water (1 mL) was stirred at RT for 16 h. The volatiles were evaporated under reduced pressure, the pH was adjusted to =3 with a 1.0N aq. solution of HCl, and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, filtered and concentrated to afford Intermediate 258E (0.05 g, 84%, a mixture of cis and trans isomers) as a yellow liquid. The crude product was used in the next step without purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.20-12.36 (m, 1H), 5.86-6.24 (m, 1H), 2.57-2.86 (m, 1H), 2.27-2.46 (m, 2H), 1.77-1.93 (m, 2H), 1.36 (s, 1H), 1.27 (s, 2H).

1. customThe volatiles were evaporated under reduced pressure
2. extractionthe aqueous layer was extracted with EtOAc (3×10 mL)
3. washThe combined organic layers were washed with water, brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-ab51ad76b05d4690a5bc6f553db22790

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273058B2