Sodium Carbonate → Methyl (S)-3-phthalimido-3-(3,4-dimethoxyphenyl)propionate

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Reaction Steps

Methyl (S)-3-amino-3-(3,4-dimethoxyphenyl)propionate (0.45 g, 1.63 mmol), sodium carbonate (0.17 g, 1.63 mmol) and N-carboethoxyphthalimide (0.36 g, 1.63 mmol) were allowed to react according to the procedure of Example 85. Methyl (S)-3-phthalimido-3-(3,4-dimethoxyphenyl)propionate was obtained as a white powder, 0.51 g (85%); 1H NMR (DMSO-d6, 250 MHz)δ 7.87 (br s, 4H, Ar), 6.80-7.10 (m, 3H, Ar), 5.65 (dd, 1H, J1 =7 Hz, J2 =9 Hz), 3.73 (s, 3H, OCH3), 3.72 (s, 3H, OCH3), 3.55 (s, 3H, OCH3), 3.30-3.67 (m, 2H); 13C NMR (DMSO-d6)δ 170.8, 167.7, 148.6, 148.4, 134.7, 131.1, 131.0, 123.2, 119.3, 111.7, 111.0, 55.5, 51.6, 49.9, 35.6. Anal. Calcd for C20H19NO6. Theoretical C, 65.03; H, 5.18; N, 3.79. Found C, 64.94; H, 5.29; N, 3.86. HPLC 97%.

Provenance & Evidence