Water → HCID 89560334, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-tert-butoxycarbonylamino-2-(2-fluoro-5-iodo-benzyl)-malonic acid diethyl ester G-22 in EtOH (113 mL) was heated to 40° C. and water (50 mL) was then added giving an easily stirrable emulsion. 1M aq. NaOH (93 mL) was carefully added and reaction mixture was heated to 100° C. for 16 h. The reaction mixture was cooled to RT and the volatiles were removed in vacuo. The remaining aqueous phase was extracted once with TBME and this extract was discarded. The aqueous layer was acidified with 25% aq. HCl and extracted with TBME (2×). The combined organic layers were washed with water, dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with a gradient of 25% to 50% EtOAc in hexane) to give the title compound as a white solid. LC-MS B: tR=0.80 min; [M-Me]+=394.95.

Provenance & Evidence