Potassium trimethylsilanolate → HCID 59581298, compound

Participants

Reaction Steps

To a stirred solution of methyl[(tert-butoxycarbonyl)(3,5-difluorobenzyl)amino]acetate from Step B (1.89 g, 5.99 mmol) in THF (60 mL) was added potassium trimethylsilanolate (1.00 g, 7.79 mmol). The reaction mixture was allowed to stir at ambient temperature for 72 hours. The bulk of the THF was then removed in vacuo, and the residue was diluted with water. The aqueous layer was extracted three times with diethyl ether, discarding ether extracts. The aqueous layer was placed under reduce pressure to remove residual ether and then was brought to an acidic pH with aqueous 1 M HCl to obtain an oil. The oil was dissolved in EtOAc and the combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound. MS: m/z=319 (M+18 (NH4+)).

Provenance & Evidence