Sodium Hydroxide → (rac.)-(1R*,5S*)-3-Acetyl-7-{6-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-6,9-dicarboxylic acid 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester

Participants

Reaction Conditions

Reaction Steps

To a sol. of compound C9 (3.03 g, 3.81 mmol) in EtOH (30 mL) was added aq. 1M NaOH (15 mL). This mixture was heated to 80° C., and stirred at this temperature for 2.5 h. The mixture was partially concentrated under reduced pressure. The residue was acidified with aq. 2M HCl, and the mixture was extracted with EtOAc. 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-acetyl-7-{6-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-7-ene-6,9-dicarboxylic acid 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester (2.70 g, quantitative yield) that was used further without purification. LC-MS: tR=1.08 min; ES+: 710.09.

Provenance & Evidence