Triethylamine → HCID 86750501, compound

Participants

Reaction Steps

A solution of 0.076 g (0.15 mmole) of trans 1-(N,N-diphenylaminocarbonyl)-4-(RS)-(N,N-dipentylaminocarbonyl)piperidine -2-(RS)-carboxylic acid (from Example 1, Step E above) and 0.022 g (0.165 mmole) of HOBt in 6 mL of dry methylene chloride at 0 deg C. under nitrogen was treated with 0.04 g (0.21 mmole) of EDAC. The cooling bath was removed and after 40 mina mixture of 0.11 g (0.3 mmole) of N-(benzyloxycarbonyl)-N-(aminocarbonylmethyl)ethylenediamine trifluoroacetic acid salt (from Example 3, Step C above) and 0.042 mL (0.3 mmole) of triethylamine in 2 mL of methylene chloride was added, and the resulting solution was stirred for 19 hr at room temperature. The mixture was then concentrated in vacuo and the residue partitioned between 20 mL of water and 30 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted with 25 mL of ethyl acetate. The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on 36 g of silica eluting with 1 L of 3:100 methanol:methylene chloride then 250 mL of 4:100 methanol:methylene chloride to give 56 mg (50%) of an oil.

Provenance & Evidence