HCID 67897689, compound → HCID 178511791, compound

Participants

Reaction Steps

A mixture of [(1,1-dimethylethoxy)carbonyl]-N-[(1S,2R)-1-(cyclohexylmethyl)-2-hydroxy-2-[1-[(phenylmethoxy)methyl]-1H-imidazol-2-yl]ethyl]-N3 -[(phenylmethoxy)methyl]-L-histidinamide (1.46 g., 2.0 mmole) [prepared as set forth in Example 11 (d)], 20% palladium hydroxide on carbon catalyst (350 mg.), and 1.0 N hydrochloric acid (4 ml., 4 mmole) in methanol (15 ml.) is hydrogenated under a slow stream of hydrogen for 20 hours at 25°, after which it is filtered and concentrated to dryness. The residue (1.1 g.) is dissolved in acetic acid (30 ml.) and dry HCl gas is bubbled through the solution for 30 minutes at 25°. The mixture is then stirred at 25° for 2 hours, after which is is concentrated in vacuo. The residue is triturated with acetonitrile to give 833 mg. of a white solid. The solid is dissolved in excess 1N hydrochloric acid and concentrated to dryness. The process is repeated three times to give N-[(1S,2R)-1-(cyclohexylmethyl)-2-hydroxy-2-(1H-imidazol-2-yl)ethyl]-L-histidinamide as a white solid.

Provenance & Evidence