(4S,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid [1-(4-methoxy-phenyl)ethyl]-amide → (4R,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of (4S,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid [1-(4-methoxy-phenyl)ethyl]-amide (Example 72d, 1.43 g) was dissolved in TFA (30 mL) and stirred at 75° C. for 1 hr. The TFA was evaporated in vacuo and the residue was then dissolved in dichloromethane (30 ml). Triethylamine (1.04 g) and trifluoroacetic acid anhydride (0.95 g) were added dropwise at 0° C. for 15 minutes. The reaction was stirred for 1 hr and the reaction mixture was washed with water (20 ml). The organic layer was dried (MgSO4), filtered, concentrated in vacuo and concentrated. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0->0/1 (v/v) as eluent.

Provenance & Evidence