Diisopropylethylamine → 1-[N-Pentyl-N-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]carbamoyl]-1,2,3,4-tetrahydroquinoline

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Reaction Steps

Following the procedure of Example 7, Step B, 1,2,3,4-tetrahydroquinoline-1-carbonyl chloride (from Step A) was reacted with 1.2 equivalents of N-pentyl-N-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]amine (from Step D) in the presence of N,N-diisopropylethylamine. Flash chromatography of the crude product on silica gel (elution with 4:1 and then 3:1 hexane-EtOAc) gave two major products. (Concentration of fractions containing the pure second product afforded a 27% yield of the title compound as a stiff foam, homogeneous by TLC in 3:1 hexane-EtOAc; FAB-MS m/e 723 (M+1)+. The 1H NMR spectrum indicated the presence of two isomeric forms.

Provenance & Evidence