1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(5-chloro-3-pyridyloxy)-N-(1-tert.butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide

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Reaction Steps

2-(5-Chloro-3-pyridyloxy)butyric acid (2.26 g), 4-amino-1-tert.-butyldimethylsilyloxy-4-methylpent-2-yne (2.27 g) and 4-dimethylaminopyridine (0.010 g) in dry dichloromethane (50 ml) were stirred at ambient temperature and N-dimethylaminopropyl-N′-ethylcarbodiimide hydrochloride (2.11 g) was added. The mixture was stirred at ambient temperature for 3 hours, stored for 18 hours, diluted with dichloromethane and washed with saturated aqueous sodium hydrogen carbonate (twice) then water (twice). The organic phase was dried over magnesium sulphate and evaporated under reduced pressure to give a dark yellow oil, 4.4 g, containing the required product.

Provenance & Evidence