Acetone → HCID 10050270, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-methyl morpholine oxide (27 mg, 0.23 mmol) and a 0.2M solution of osmium tetroxide in toluene (5 μL, 0.001 mmol) in acetone (0.5 mL) and water (0.5 mL) was treated with 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-vinyl-pyrazin-2-yl)-propionamide (prepared as in Example 54, 50 mg, 0.115 mmol). Two drops of tetrahydrofuran were added to fully dissolve the substrate, and the resulting mixture was stirred at 25° C. overnight. The reaction mixture was concentrated in vacuo, and the residue was treated with water (10 mL) and methylene chloride (25 mL). The organic phase was washed with a 1 N aqueous hydrochloric acid solution (10 mL), and each aqueous phase was extracted with a small portion of methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(1,2-dihydroxy-ethyl)-pyrazin-2-yl]-propionamide (48 mg) as a colorless foam: (ES)+-HRMS m/e calcd for C21H26N3O5S (M+H)+ 468.1355, found 468.1357.

Provenance & Evidence