Hydrochloric Acid → HCID 53696547, compound

Participants

Reaction Steps

A mixture of (±)-N-[2-[3-(cyclopropylmethoxy)-4-methoxyphenyl]-2-[(trimethylsilyl)-oxy]ethyl]-N-(dimethoxyethyl)urea (39.6 g) and HCl (150 ml) in methanol (450 ml) was stirred for 48 hours at RT. The resulting mixture was concentrated and the concentrate (150 ml) was extracted three times with CH2Cl2. The combined organic layer were poured out into a NaOH solution. The mixture was stirred and the layers were separated. The aqueous phase was extracted twice with CH2Cl2. The separated organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from ethylacetate/diisopropyl ether. The precipitate was filtered off and dried, yielding 10.36 g (37.9%) of 1-[2-[3-(cyclopropylmethyloxy)-4-methoxyphenyl]-2-hydroxy-ethyl]-1,3-dihydro-2H-imidazol-2-one (interm. 6).

Provenance & Evidence