Diisopropylethylamine → (S)-2-(2-Allyloxy-benzoylamino)-3-(4-allyloxy-3-chloro-phenyl)-propionic acid methyl ester

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Reaction Conditions

Reaction Steps

In a 10 mL round-bottomed flask, (S)-methyl 3-(4-(allyloxy)-3-chlorophenyl)-2-aminopropanoate (65 mg, 241 μmol, Eq: 1.00) was combined with DMF (2 mL) to give a colorless solution. 2-(allyloxy)benzoic acid (54.2 mg, 289 μmol, Eq: 1.20), HATU (183 mg, 482 μmol, Eq: 2.00) and Hunig's base (62.3 mg, 84.2 μL, 482 μmol, Eq: 2.00) were added. The reaction mixture was stirred at 22° C. for 16 h. The reaction mixture was poured into saturated aqueous NaHCO3 solution and extracted with DCM (2×). The organic layers were combined, washed with 0.1M aqueous HCl (1×), water (3×), and brine (1×). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, n-heptane/AcOEt 4/1) to yield a light yellow oil (96 mg; 93%). m/z=430.2 [M+H]+.

Provenance & Evidence