Sodium Thiosulfate → HCID 9916656, compound

Participants

Reaction Steps

A solution of N-[(S)-1-(1-Benzooxazol-2-yl-1-hydroxy-methyl)-butyl]-3-benzylsulfonyl-2-benzylsulfonylmethyl-propionamide (0.140 g, 0.234 mmol) in methylene chloride (5 mL) was treated with 1,1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane) (0.127 g, 0.30 mmol.) and the resulting solution was stirred at room temperature for 30 minutes. Aqueous sodium thiosulfate and sodium bicarbonate (15 mL, 0.25 M) were added and the reaction mixture was stirred for 20 minutes. The product was extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure and the residue was crystallized from t-butylmethyl ether to give N-[(S)-1-(1-benzooxazol-2-yl-methanoyl)-butyl]-3-benzylsulfonyl-2-benzylsulfonylmethyl-propionamide (0.103 g, 74%); NMR (DMSO): 9.15 (d, J=6 Hz, 1H); 8.01 (d, J=7 Hz, 1H); 7.89 (d, J=8 Hz, 1H); 7.65 (t, J=7 Hz, 1H); 7.54 (t, J=8 Hz, 1H); 7.37 (m, 10H); 5.36 (m, 1H); 4.5 (m, 4H); 3.68 (m, 1H); 3.45–3.25 (m, 4H); 1.95 (m, 1H); 1.73 (m, 1H); 1.47 (m, 2H); 0.91 (t, J=7 Hz, 3H); MS: M(H+) 597.0 (596.17);

Provenance & Evidence