Triethylamine → HCID 22182443, compound

Participants

Reaction Steps

A solution of {(4-benzyloxy-benzenesulfonyl)-[2-benzyloxycarbonylamino-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propyl]-amino}-acetic acid methyl ester (compound of formula LIII, 1.3 g, 2.0 mmol) in 75 ml of ethanol was treated with triethylamine (0.28 ml, 0.20 g, 2.0 mmol) and 0.2 g of 10% palladium on carbon. After stirring for about 2 hours under 1 atmosphere of hydrogen, the mixture was filtered through a pad of Celite® and concentrated in vacuo. The residue was dissolved in 10 ml of toluene, diluted with 3 ml of methanol and was refluxed for about 1.5 hours. Concentration of the mixture in vacuo afforded 0.6 g of 4-(4-hydroxy-benzenesulfonyl)-6-methyl-5-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-piperazin-2-one (compound of formula LIV). A compound of the formula LI can be converted to a compound of the formula LIII by the method of Step 42 that, in turn, can be converted to a compound of Formula I according to the procedure of Step 43.

Provenance & Evidence