Phenol → (2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

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Reaction Steps

A solution of (2S)-3-[4-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (Example 284, Step 2) (0.1 mmol, 32 mg) in 0.7 ml of DM in a 16×100 mm tube was treated with phenol (0.15 mmol, 15 mg), cesium carbonate (0.3 mmol, 95 mg). The mixture was stirred at room temperature overnight and the reactants were filtered and washed with DMF a several times. The solvent was evaporated under vacuum, and the residue was reconstituted in a mixture of ethanol (2 ml) and NaOH (1M, 1 ml), which was stirred at room temperature until temperature until reaction was completed by HPLC-MS. Upon completion, HCl (1M) was added pH=3) and the solvents were eliminated under vacuum. The residue was reconstituted in CH2Cl2/H2O and filtered through a hidrofobic syringer. The organic layer was separated, concentrated and purified by HPLC-MS to afford the title compound as a colorless oil. MS (ES) for C19H22O5 [M+NH4]+: 348.4.

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