Lithium hydroxide, monohydrate → Ethyl-N-(2-carboxyphenoxy)acetimidate

Participants

Reaction Steps

LiOH.H2O (431 mg, 10.3 mmol) was added to a solution of ethyl-N-(2-benzyloxycarbonylphenoxy)acetimidate 18 (802 mg, 2.56 mmol) in a 9/3/3 mL mixture of THF/MeOH/H2O and the reaction was stirred at room temperature. After 6 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 (4×30 mL). The combined organics were washed with H2O (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to afford 20 as a white solid (459 mg, 80%). 1H-NMR (500 MHz, d6-Acetone) δ 1.34 (t, J=6.9 Hz, 3H), 2.18 (s, 3H), 4.20 (q, J=6.9 Hz, 2H), 7.02 (ddd, J=0.9, 7.3, 7.8 Hz, 1H), 7.51 (ddd, J=1.8, 7.3, 8.7 Hz, 1H), 7.60 (dd, J=0.9, 8.7 Hz, 1H) 7.86 (dd, J=1.8, 7.8 Hz, 1H); 13C-NMR (125 MHz, d6-Acetone) δ 14.6, 14.7, 63.8, 115.2, 118.5, 121.3, 132.4, 134.5, 160.2, 166.8, 167.4; ESI-MS 224 m/z [MH]+, C11H14NO4 requires 224.

Provenance & Evidence