PRODUCTION OF OPTICALLY ACTIVE AMIDE COMPOUNDS

摘要

PROBLEM TO BE SOLVED: To obtain the optically pure amide compound in a high yield in short reaction steps from industrially available tetrahydroisoquinoline-3(S)-carboxylic acid as a raw material. SOLUTION: (A) Tetrahydroisoquinoline-3(S)-carboxylic acid of formula I is reacted with (B) either of phosgene, phosgene dimer and triphosgene to obtain the N-carboxy anhydride of formula II, which is reacted with (D) either of ammonia and a 1-6C lower primary amine. The obtained derivative of formula III can be reduced in the presence of a metal catalyst (preferably Ru) to obtain a derivative of formula IV. The derivative of formula IV has an excellent HIV protease-inhibiting activity and is useful as an intermediate for saquinavir (EP 432694) having an excellent HIV protease-inhibiting activity and expected as an anti AIDS medicine.