Lithium Hydroxide → HCID 22988677, compound

Participants

Reaction Steps

2-Ethoxy-3-[4-(2-{4-(isopropylaminocarbonyl)phenyl}ethoxy)phenyl]propanoic acid ethyl ester (described in Example 106) (1 g; 2.34 mmole) was dissolved in tetrahydrofuran (10 ml). Lithium hydroxide (0.056 g; 2.34 mmole) dissolved in water (6 ml) was added slowly in portions during 20 minutes. The reaction mixture was stirred at room temperature for 3 hours and then diluted with water followed by careful evaporation of tetrahydrofuran. The residual water phase was extracted once with diethyl ether, then acidified and extracted with ethyl acetate. The ethyl acetate phase was washed with brine, dried with sodium sulfate and evaporated. The residue was dissolved in methanol (10 ml) and sodium hydroxide (0.109 g; 1.73 mmole) in water (3.5 ml) was added. The solution was evaporated and the residue redissolved in water. Freeze drying gave 0.643 g (65.2% yield) of 2-ethoxy-3-[4-(2-{4-(isopropylaminocarbonyl)phenyl}ethoxy)phenyl]propanoic acid.

Provenance & Evidence