Triethylamine → HCID 42599204, compound

Participants

Reaction Steps

(Method J8) To a solution of appropriate carboxylic acid 1/58, 1/59, 1/60, 1/61 (2.0 mmol) in anhydrous tetrahydrofuran (5 ml) under argon atmosphere triethylamine (0.36 ml, 2.6 mmol) was added and the mixture was cooled in an ice bath. Then to the reaction mixture iso-butylchloroformate (0.3 ml, 2.3 mmol) was added and the resulting mixture was stirred for 20 min at ice bath temperature. At the same time, a suspension of methyl 6-aminocaproate hydrochloride (2c) (364 mg, 2 mmol), anhydrous tetrahydrofuran (3 ml) and triethylamine (0.31 ml, 2.2 mmol) was prepared and stirred for 20 min at room temperature. This suspension to the above prepared reaction mixture of activated ester was added. The resulting mixture was stirred at ice bath temperature for 15 min and 1 hour at room temperature, then diluted with brine (50 ml) and extracted with ethyl acetate (3×25 ml). The organic phase was washed with brine, 5% NaHCO3, brine, saturated KH2PO4 and brine. The organic layer was dried (Na2SO4) and the solvent was evaporated. The residue was purified on silica gel (20 g) with chloroform-ethyl acetate as eluent affording title products 3/58, 3/59, 3/60, 3/61.

Provenance & Evidence