1-Hydroxybenzotriazole → HCID 86588741, compound

Participants

Reaction Steps

To a solution of 2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-4-propanesulfonyl-1,4-thiazepin-7-yl]acetic acid (3.95 g) in dimethylformamide (DMF) (40 ml) were added N-(2-tetrahydropyranyloxy)amine (1.30 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC; 1.82 g), and 1-hydroxybenzotriazole (HOBt; 1.28 g) at 0° C. The resulting mixture was stirred for 3 hours at room temperature. Ethyl acetate (500 ml) was added and the solution was washed with water (300 ml×3), saturated sodium bicarbonate, and brine, dried over magnesium sulfate, and evaporated to give a pale yellow solid. Silica gel column chromatography (eluent: 0 to 0.3% methanol in chloroform) afforded N-(2-tetrahydropyranyloxy)-2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-4-propanesulfonyl-1,4-thiazepin-7-yl]acetamide (4.34 g) as a pale yellow solid.

Provenance & Evidence