Diisopropylethylamine → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-tert-butoxycarbonyl-3-piperidinol

Participants

Reaction Conditions

Reaction Steps

To the solution of tert-butyl 4-amino-3-hydroxypiperidin-1-carboxylate (20 g, 92 mmol) obtained in step 4 of Preparation Example 1 and 1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarboxylic acid (5.0 g) obtained in Step 2 in 70 ml of dimethylformamide, were added hydroxybenzotriazole(HOBt; 3.1 g, 23.1 mmol) and diisopropylethylamine (DIEA; 9.0 ml, 53.4 mmol). The reaction mixture was cooled to 0° C. and was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC-HCl; 5.1 g, 26.7 mmol) thereto. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was diluted with 200 ml of ethyl acetate, washed with 10% citric acid solution, a saturated sodium bicarbonate solution and brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 4.3 g of the titled compound.

Provenance & Evidence