Hydrogen chloride-ethyl acetate → HCID 86755913, compound

Participants

Reaction Steps

A mixture of(R)-N2 -(Boc)-N5 -(Cbz)-(R or S)-N-[1-carbamoyl-(4-methoxy-phenyl)methyl]ornithine amide and (R)-N2 -(Boc)-N5 -(Cbz)-(S or R)-N-[1-carbamoyl(4-methoxyphenyl)methyl]ornithine amide (4.5 g; 8.5 mmol) was dissolved in 25 mL of MeOH and 100 mL of HCl/EtOAc was added. The mixture was magnetically stirred at room temperature for 1 hour, then evaporated at reduced pressure to give a crude hydrochloride salt of the diastereomers of (R)-N5 -(Cbz)-(R or S)-N-[1-carbamoyl-(4-methoxy-phenyl)methyl]ornithine amide and (R)-N5 -(Cbz)-(S or R)-N-[1 -carbamoyl-(4-methoxyphenyl)methyl]ornithine amide hydrochloride. Crystallization from MeOH:EtOAc provided 1.3 g of the more polar sub-title diastereomer (32%).

Provenance & Evidence