Acetic Acid → HCID 53902176, compound

Participants

Reaction Steps

To a solution of 11.5 g. of 1-(4-benzoylbutyryl)-L-proline (Example 41) in 115 ml. of acetic acid is added dropwise a solution of 6.4 g. of bromine in 25 ml. of acetic acid. The mixture is stirred for 18 hours, reduced to 1/3 its volume, poured into ice and water and extracted with dichloromethane. The organic extract is washed with water and saline, dried over magnesium sulfate and evaporated in vacuo to a yellow gum. This gum is dissolved in dichloromethane, placed on a 11/2"×24" column of silica gel which has been wet with dichloromethane and eluted with ethyl acetate:acetic acid (1:1) taking 100 ml. cuts. Cut number 7 gives 2.1 g. of solid which is dissolved in dichloromethane, filtered through celite and evaporated to dryness giving the desired product as 2.0 g. of an orange gum.

Provenance & Evidence