Sodium hydride → HCID 58387150, 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 (18.0 mg, 60% suspension in mineral oil, 0.45 mmol). In a separate vial, a solution of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (79.0 mg, 0.600 mmol) in THF (2.0 mL) was combined with a solution of compound 49-2 (138.0 mg, 0.300 mmol), and added dropwise to the 20 mL scintillation vial containing NaH. The resulting mixture was stirred at rt for 5 min, then cooled in a ice bath (0° C.) and quenched by a dropwise addition of water (6 mL). The mixture was allowed to warm up to rt and stirring was maintained for 5 min. The mixture was acidified with 5% aqueous HCl and extracted with EtOAc (three times, 3 mL). The organic layers were combined and evaporated to dryness in vacuo. The residue was dissolved in ACN (4 mL) and added to a vial containing 5% aqueous LiOH (1 mL). The resulting mixture was stirred at 65° C. for 1 h, then acidified with 5% aqueous HCl and extracted with EtOAc (three times, 3 mL). The organic layers were combined and evaporated to dryness in vacuo. The crude product was used in the next step without further purification. LR-MS (API-ES): mixture of two N-SEM isomers, calculated for C26H31ClN2O4Si 498.2, observed m/e 499.0 (M+H)+ (Rt 3.78. 3.87 min).

Provenance & Evidence