Sodium Thiosulfate Pentahydrate → HCID 86660405, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(2-fluoro-5-nitro-phenyl)-3-hydroxy-1-methyl-propyl]-amide (intermediate A4C) (1.1 g, 3.3 mmol) in anhydrous CH2Cl2 (35 ml) at 23° C. was added Dess-Martin Periodinan (1.825 g, 4.3 mmol) and the mixture was stirred at 23° C. for 3 h. Reaction mixture was poured into 20 mL of a 1M aqueous NaHCO3 solution containing 2 g of sodium thiosulfate, pentahydrate and the mixture was stirred at 23° C. for 15 min. The two phases were separated, the collected organic phase was dried over Na2SO4 and removal of the solvent in vacuum left a residue. Purification of the residue was performed by chromatography on silica using a mixture of Heptane and a solution of 3% Triethylamine in Ethylacetate which yielded the (R)-2-Methyl-propane-2-sulfinic acid [(S)-1-(2-fluoro-5-nitro-phenyl)-1-methyl-3-oxo-propyl]-amide (970 mg, 47.7 mmol, 88% yield) as a off-white solid. MS (ISP): m/z=331.1 [(M+H)+].

Provenance & Evidence