N-Iodosuccinimide → HCID 118274330, compound

Participants

Reaction Steps

To a solution of Example 14A (22.4 g, 92 mmol) in acetonitrile (1 L) under nitrogen was added N-iodosuccinimide (21.84 g, 97 mmol) at ambient temperature. After stirring approximately 1 hour the reaction was complete. Solids started to crash out of the mixture and they were filtered off and washed with acetonitrile to provide the title compound as a solid. The filtrate was concentrated, mixed with 50 mL of dichloromethane, and sonicated for 30 minutes. Some solid did not dissolve and was filtered, washed with dichloromethane, and dried to give additional title compound. The filtrate was purified on an Analogix MPLC using a silica gel column eluting with 30-40% ethyl acetate/heptanes to give additional title compound. MS (ESI+) m/z 369.0 (M+H)+.

Provenance & Evidence