Lithium hydroxide, monohydrate → Ethyl-N-(4-carboxyphenoxy)acetimidate

Participants

Reaction Steps

LiOH.H2O (550 mg, 13.1 mmol) was added to a solution of ethyl-N-(4-benzyloxycarbonylphenoxy)acetimidate 19 (1.04 g, 3.32 mmol) in a 9/3/3 mL mixture of THF/MeOH/H2O and the reaction was stirred at room temperature. After 24 h the reaction was diluted with H2O (100 mL), washed with CH2Cl2 (4×30 mL), acidified to pH˜5.0-5.5 with 0.5 N HCl, and extracted with EtOAc (3×30 mL). The combined organics were washed with H2O (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to afford 21 as a white crystalline solid (698 mg, 94%). 1H-NMR (500 MHz, CDCl3) δ 1.37 (t, J=6.9 Hz, 3H), 2.14 (s, 3H), 4.22 (q, J=6.9 Hz, 2H), 7.18-7.22 (m, 2H), 8.04-8.08 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 14.5, 14.6, 63.3, 113.7, 122.1, 132.3, 164.2, 166.7, 172.0; ESI-MS 224 m/z [MH]+, C11H14NO4 requires 224.

Provenance & Evidence