Sodium Thiosulfate → HCID 23648438, compound

Participants

Reaction Steps

To a solution of 50.5 mg (0.084 mmol) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate in 2.2 mL of chloroform was added 44.6 mg (0.105 mmol) of Dess-Martin periodinane. The mixture was stirred at room temperature for 1.25 h, and then diluted with ethyl acetate. A saturated aqueous sodium thiosulfate solution was added, and the two layers were mixed vigorously before a saturated aqueous solution of sodium bicarbonate was added. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography eluting with a hexane:acetone solution (1:1) to yield 19 mg (38%) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{[(2-pyridinylsulfonyl)amino]acetyl}pentylcarbamate. ES-LCMS m/z 598 (M+H)+ retention time=4.00 min. HRMS C26H33Cl2NS5O5S m/z 598.1658 (M+H)Cal; 598.1674 (M+H)Obs.

Provenance & Evidence