Hydrochloric Acid → HCID 67092976, compound

Participants

Reaction Conditions

Reaction Steps

Solutions of sodium chlorite (66 mg, 0.58 mmol in 0.5 mL water) and 10% aq. sodium hypochlorite (4 μL, 6 μmol in 0.2 mL water) were added simultaneously at 35° C. to a mixture of (3S,6S)-3-(2-hydroxy-ethyl)-6-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyrazine-7-carboxylic acid benzyl ester (98 mg, 0.29 mmol), 2,2,6,6-tetramethylpiperidine-1-oxyl radical (3 mg, 20 μmol) in 1 M aq. potassium phosphate buffer (pH 6.85; 0.75 mL) and acetonitrile (1 mL). The reaction mixture was heated at 45° C. for 16 h, then cooled to 0° C., diluted with water and EtOAc and treated with 1 M sodium thiosulfate solution. The pH was then set to 3-4 by addition of 2 M aq. hydrochloric acid solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; DCM→DCM/MeOH/25% aq. ammonia solution 90:10:0.25) afforded the title compound (84 mg, 82%). Colourless gum, MS: 347.1 (M−H)−.

Provenance & Evidence