Sodium Hydroxide → HCID 131728984, compound

Participants

Reaction Conditions

Reaction Steps

Compound C2 (3.82 g, 6.80 mmol) was dissolved in EtOH (100 mL). The sol. was heated to 70° C., and aq. 1M NaOH (80 mL, 80 mmol) was added. The mixture was stirred at 80° C. for 3 h, and allowed to cool to rt. The solvents were partially removed under reduced pressure, and the residue was poured into a separatory funnel filled with EtOAc. Aq. 1M HCl was added until the aq. phase was acidic, and the phases were shaken and separated. The aq. layer was extracted with EtOAc (2×), and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound mixed with (rac.)-(1R*,5S*)-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-8-aza-bicyclo[3.2.1]oct-3-ene-2,8-dicarboxylic acid 8-tert-butyl ester (3.45 g, 93%) that was used further without purification. LC-MS: tR=1.13 min; ES+: 548.25.

Provenance & Evidence