1-Hydroxybenzotriazole → HCID 22276506, compound

Participants

Reaction Steps

To a solution of 2-[7-(5-bromo-2-thienyl)-4-(9-fluorenylmethoxycarbonyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetic acid (400 mg), O-(2-tetrahydropyranyl)-hydroxylamine (95.2 mg) and 1-hydroxybenzotriazole (110 mg) in N,N-dimethylformamide (10 ml) was added WSCD-HCl (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) (156 mg) at room temperature. After being stirred at the same temperature overnight, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (30 ml) and the solution was washed successively with 5% aqueous citric acid solution, a saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent; 1% MeOH in chloroform (CHCl3)) to afford N-(2-tetrahydropyranyloxy)-2-[7-(5-bromo-2-thienyl)-4-(9-fluorenylmethoxycarbonyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (313 mg) as an amorphous powder.

Provenance & Evidence