Sodium Carbonate → Methyl 2-ethoxycarbonylamino-3,3-diphenylpropanoate

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Reaction Steps

To a solution of methyl 2-amino-3,3-diphenylpropanoate hydrochloride (Example 1a, 28.0 g, 96 mmol), chloroform (250 ml), and 1.0M sodium carbonate (250 ml) was added ethyl chloroformate (9.20 ml, 96 mmol). After the solution had been stirred for 18 h the organic phase was separated, washed with 10% citric acid, water, saturated brine and dried (MgSO4). After removal of the solvent in vacuo the residue was recrystallised from hot methanol to give methyl 2-ethoxycarbonylamino-3,3-diphenylpropanoate, m.p.=107°-109° C. 1H NMR (250 MHz, CDCl3) δ7.18-7.33 (10H, m), 5.12 (1H, br t, J=8.5 Hz), 4.95 (1H, br d, J=8.5 Hz), 4.40 (1H, d, J=8.0 Hz), 4.06 (2H, q, J=7.0 Hz), 3.50 (3H, s), 1.17 (3H, t, J=7.0 Hz). m/z (CI+) 328(MH).

Provenance & Evidence