4-Benzylphenol → (2S)-3-{4-[5-(4-Benzyl-phenoxy)-pent-1-ynyl]-phenyl}-2-methoxy-propionic acid

Beteiligte Stoffe

Reaktionsschritte

A solution of 3-[4-(5-Bromo-pent-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester from Step A (0.1 mmol, 1 eq) in 0.7 ml of DMF in a 16×100 mm tube treated with 4-hydroxydiphenylmethane (0.11 mmol, 1.1 eq) and Cesium Carbonate (0.3 mmol, 3 eq) and stirred at room temperature overnight. The reactants were filtered and washed with DMF several times. The solvent was evaporated under vacuo and the residue reconstituted in a mixture of Ethanol (2 ml) and NaOH (1M) (1 ml) and stirred at room temperature until reaction is completed by HPLC-MS. Then HCl (1M) was added (until pH=3) and the solvent were eliminated under vacuo. 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 get the title compound. MS(ES) for C28H28O4[M+NH4]+: 446.2.

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