Diisopropylethylamine → HCID 86753076, compound

Participants

Reaction Steps

The product of step 1 (0.116 g), EDC hydrochloride (0.076 g, 1.1 equivalent), hydroxybenzotriazole (0.054 g, 1.1 equivalent), and diisopropylethylamine (0.143 g, 3 equivalent) are mixed with dichloromethane (20 mL) to give a homogeneous solution. Hydroxylamine hydrochloride (0.051 g, 2 equivalent) is added as a solid. DMF (3 mL) is added to solubilize the hydroxylamine hydrochloride. The reaction is allowed to stir at room temperature overnight. The solvents are then removed under reduced pressure and the residue partitioned between ethyl acetate and 1N HCl. The organic phase is separated and the aqueous phase re-extracted with ethyl acetate. The combined organic phases are dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product is loaded onto a reverse phase column as a DMSO solution. The column is eluted with a step gradient, starting at 20% acetonitrile/water, and raised in 10% increments. The appropriate fractions are combined to give 22 mg of the title compound. 1H NMR (DMSO, 300 MHz): 10.4, 7.69-7.65, 7.43, 7.01-6.98, 3.80, 1.20-1.17, 0.77, 0.75, 0.69 .

Provenance & Evidence