Sodium Hydroxide → HCID 86620046, compound

Participants

Reaction Conditions

Reaction Steps

The intermediate from example 1 step H (4.57 g, 6.22 mmol) was dissolved in a 1:1 mixture of methanol/ethanol (60 mL) followed by the addition of 5 N NaOH (12.0 mL). The vessel was heated to 45° C. for 1 hr. The reaction mixture was cooled to ambient temperature and diluted with 400 mL EtOAc. The EtOAc solution was washed twice with 2 N NaOH, dried over Na2SO4, filtered through a fritted funnel and concentrated in vacuo. The crude residue was purified on silica gel and eluted a combination of EtOAc/hexanes (1-30% EtOAc/hexanes linear gradient). This provided the title compound. 1H-NMR (CDCl3): δ 1.38 (d, 3H, J=6.5 Hz), 1,90-2.22 (m, 2H), 2.34-2.42 (m, 1H), 2.72 (dd, 1H, J=8.5, 10.5 Hz), 3.12-3.18 (m, 1H), 3.24-3.31 (m, 1H), 3.46-3.56 (m, 2H), 3.55-3.62 (m, 1H), 3.65-3.74 (m, 1H), 4.09 (dd, 1H, J=4.0, 11.5 Hz), 4.21 (d, 1H, J=8.5 Hz), 4.31 (s, 21H), 4.96 (q, 1H, J=6.5 Hz), 6.90-7.02 (m, 4H), 7.14-7.22 (m, 4H), 7.25-7.34 (m, 3H), 7.69 (s, 1H) ppm.

Provenance & Evidence