Nitric Acid → HCID 70654349, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (3aR,8S,8aS)-rel-8-(2-fluoro-phenyl)-8-methyl-4,4-dioxo-3,3a,4,5,8,8a-hexahydro-1H-2-oxa-4λ6-thia-7-aza-azulen-6-ylamine (110 mg, 176 μmol) in trifluoroacetic acid (1.33 g, 11.7 mmol) was cooled to 0-5° C. Sulfuric acid (149 mg, 81.2 μl, 1.52 mmol), then nitric acid (12.1 mg, 8.01 μl, 192 μmol) was added slowly. The reaction mixture was stirred at 0° C. for 1 hour. In order to complete the reaction, another equivalent of nitric acid (12.1 mg, 8.01 μl, 192 μmol) was added and stirring continued at 0° C. for 2 hours. For the workup, ice-water was added to the reaction mixture, and the resulting suspension was set to pH ˜12 by addition of a solution of sodium hydroxide (32%). The mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulphate and evaporated. The crude (3aR,8S,8aS)-rel-8-(2-fluoro-5-nitro-phenyl)-8-methyl-4,4-dioxo-3,3a,4,5,8,8a-hexahydro-1H-2-oxa-4λ6-thia-7-aza-azulen-6-ylamine was obtained as a brown solid and was engaged in the next step without purification. MS (ISP): m/z=358.3 [M+H]+.

Provenance & Evidence