Water → HCID 89507622, compound

Participants

Reaction Steps

49 mg (1.22 mmol) of sodium hydride were added to a solution of 200 mg (1.12 mmol) of 2-(hydroxyimino)-N-methyl-2-phenylacetamide (only Z diastereoisomer in 5 ml of DMF, and the suspension was stirred for 30 minutes at room temperature. Then, a solution of 268 mg (1.12 mmol) of but-3-in-1-yl[6-(chloromethyl)pyridin-2-yl]carbamate in 5 ml was added. The mixture was stirred for 3.5 hours at room temperature and then poured into 70 ml of water and admixed with 50 ml of AcOEt. The organic phase was separated off and dried over MgSO4. After removing the solvent, this gave 388 mg (95% purity, 88:12 mixture of Z and E diastereoisomers) of but-3-yn-1-yl{6-[({[2-(methylamino)-2-oxo-1-phenylethylidene]amino}oxy)methyl]pyridin-2-yl}-carbamate.

Provenance & Evidence