ChemInform Abstract: Synthesis of 4‐Amino‐5H‐1,2‐oxathiole 2,2‐Dioxides by Cyclization of Cyanohydrin Mesylates. New Routes to β‐Amino‐ and β‐Keto Sulfonic Acids.

Abstract

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4-Benzyloxy-γ-Sultone Derivatives: Discovery of a Novel Family of Non-Nucleoside Inhibitors of Human Cytomegalovirus and Varicella Zoster Virus

“…(()-2-Ethyl-2-(methanesulfonyloxy)butyronitrile (5c). 29 3-Pentanone (0.34 g, 4 mmol) was reacted with trimethylsilyl cyanide for 3 h. The mixture was reacted with methanesulfonyl chloride for 2 h to give 0.52 g (73%) of 5c as a white amorphous solid. MS (()-2-Cyano-2-(methanesulfonyloxy)-1,2,3,4-tetrahydronaphthalene (5h).…”

“…4-Amino-5,5-diethyl-5H-1,2-oxathiole-2,2-dioxide (6c). 29 A solution of 5c (0.36 g, 2 mmol) in dry acetonitrile was treated with cesium carbonate for 2 h to give 0.24 g (70%) of 6c as a white solid; mp (ethanol/water) 163-164 °C (lit. 29 Synthesis of Compounds 7a-h: General Procedure.…”

“…29 A solution of 5c (0.36 g, 2 mmol) in dry acetonitrile was treated with cesium carbonate for 2 h to give 0.24 g (70%) of 6c as a white solid; mp (ethanol/water) 163-164 °C (lit. 29 Synthesis of Compounds 7a-h: General Procedure. A solution of the appropriate β-amino-γ-sultone derivative 6a-h (1.1 mmol) in 4.5 N HCl in methanol (1.6 mL, 7.2 mmol) was stirred at room temperature for 16 h. Then, a solution of 1 N NaOH in methanol was added until pH ∼ 6, salts were filtered, and the solvent was evaporated.…”

“…5,5-Diethyl-4-oxo-1,2-oxathiolane-2,2-dioxide (7c). 29 Compound 6c (0.18 g, 1 mmol) was reacted with 4. Alkylation of β-Keto-γ-sultone Derivatives: General Procedure.…”

“…A solution of 5c (0.36 g, 2 mmol) in dry acetonitrile was treated with cesium carbonate for 2 h to give 0.24 g (70%) of 6c as a white solid; mp (ethanol/water) 163−164 °C (lit . 162−164 °C).…”