4-Chlorophenyl Isocyanate → (4-Chlorophenylaminocarbonyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Beteiligte Stoffe

Reaktionsschritte

To a suspension of (D,L) 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (500 mg, 2.59 mmol) in DMF (12 mL), 4-chlorophenyl isocyanate (400 mg, 2.60 mmol) was added. The reaction mixture was stirred at room temperature overnight, and the suspension became clear solution. It was then concentrated in vacuo. The residue was dissolved in CH2Cl2, and the product was extracted with 5N NaOH. The alkaline solution was then separated, acidified with 4N HCl to pH 2-3. The cloudy mixture was extracted with EtOAc. The EtOAc solution was dried over Na2SO4, concentrated in vacuo to give the titled compound as a solid (841 mg), which was pure enough for the next reaction.

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