Hydrochloric Acid → HCID 67340021, compound

Participants

Reaction Steps

A 20 mL scintillation vial equipped with a septum cap and a magnetic stirring bar was charged under N2 with NaH (6.0 mg, 60% suspension in mineral oil, 0.15 mmol). A solution of hydroxyacetic acid methyl ester (18.0 mg, 0.200 mmol) in THF (2.0 mL) was added dropwise to the vial and the resulting mixture was stirred at rt for 10 min. Then, a solution of 5-biphenyl-4-yl-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (compound 46-1, 51.3 mg, 0.100 mmol) in THF (1 mL) was added. The resulting mixture was stirred at rt for 10 mM, then diluted by dropwise addition of 1:1 ACN/water (2 mL) and left to stir at rt for 30 min. The reaction mixture was then diluted with water (5 mL), acidified with 5% aqueous HCl and extracted with EtOAc (three times, 3 mL). The organic layers were combined and washed with 5% aqueous HCl and water, and evaporated to dryness in vacuo to give the title compound as pale yellow solid. LR-MS (API-ES): mixture of two N-SEM isomers, calculated for C27H29ClN2O4Si 508.2, observed m/e 509.0 [(M+H)+, 100%], 465 (Rt 3.74 min). The compound was used in the next step without further purification.

Provenance & Evidence