Triethylamine → 1-(N-(3-(4-hydroxyphenyl)propionyl)-2-aminoethyl)-4-(2-aminoethyl)imidazole

Participants

Reaction Steps

The following materials are introduced into a reaction vessel: 5 mg (0.02 mmol) of compound VII dissolved in 0.5 ml methylene chloride; 2.8 μl (0.02 mmol) of triethylamine; and last 5.3 mg (0.02 mmol) of N-succinimidyl-3-(4-hydroxyphenyl)propionate dissolved in 0.5 ml of methylene chloride. The solution is stirred for 2 hours at room temperature and then evaporated. The residue is dissolved in 0.5 ml of trifluoroacetic acid, and hydrolysis is allowed to proceed for 1 hour and 15 minutes at room temperature. The solution is evaporated, the residue then being separated on a reversed-phase column PepRPC (Pharmacia AB) with an 0.1% trifluoroacetic acid - acetonitrile gradient. At about 7% acetonitrile compound XIX is eluted. The structure has been confirmed by NMR analysis, the NMR data being the following: 2H-imidazole 8.3, 5H-imidazole 7.2, O-H-hydroxyphenyl 7.1, m-H-hydroxyphenyl 6.85, 1-CH2 -imidazole 4.15, --CH2NHCO 3.55, --CH2N + H3 3.25 t, 4-CH2 -imidazole 3.05 t, p-CH2 -hydroxyphenyl 2.75 t, --CH2CO 2.5 t.

Provenance & Evidence