1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53638145, compound

Participants

Reaction Steps

N-tert-Butyloxycarbonylpiperidin-4-carboxylic acid (97 mg; 0.424 mmol) was dissolved in methylene chloride (2 ml). HOAt (58 mg; 0.424 mmol) and EDAC (85 mg; 0.444 mmol) were added. The reaction mixture was stirred 15 min at RT. (2R)-2-Methylamino-3-(2-naphthyl)-N-((1R)-2-(2-naphthyl)-1-thiocarbamoylethyl)propionamide (17 mg; 0.386 mmol) was dissolved in methylene chloride (2 ml) and added. Diisopropylethylamine (0.073 ml; 0.424 mmol) was added and the reaction mixture was stirred 12 hours at room temperature. Tert-butylmethylether (25 ml) was added and the reaction mixture was washed with water (25 ml), aqueous sodium hydrogencarbonate (15 ml), aqueous sodiumhydrogensulfate (10%; 15 ml), water (15 ml) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (3.5×30 cm) using gradient elution, starting with ethyl acetate/heptane (1:1) increasing to ethyl acetate/heptane (2:1) to afford 0.190 g of 4-(N-methyl-N-((1R)-2-(2-naphtyl)-1-((1R)-2-(2-naphthyl)-1-thiocarbamoylethylcarbamoyl)ethyl)carbamoyl)piperidine-1-carboxylic acid tert-butylester.

Provenance & Evidence