Dicyclohexylcarbodiimide → L-Phenylalanine

Participants

Reaction Steps

L-Phenylalanine hydrochloride (1.75 mmoles, 380 mg), diisopropylethylamine (1.93 mmoles, 0.34 ml), 2-[5-[2-(2H-tetrazol-5-yl)phenyl]-1H-benzimidazol-1-yl]octanoic acid (1.24 mmoles, 0.50 g), hydroxybenzotriazole (1.36 moles mg) and dicyclohexylcarbodiimide (1.36 mmoles, 280 mg) were reacted as in Example 37. The stereoisomers were separated by chromatography over silica gel eluted which 2% methanol in chloroform. The isomers were hydrolyzed as in Example 37 to yield N-[| -oxo-2-[5-[2-(2H-tetrazole-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-phenylalanine. Isomer A: 187 mg (MS) M. Pt.: Dec. 165° C. Calculated for C31H33N7O3.0.9 HCl: C, 63.75; H, 5.85; N, 16.79. Found: C, 63.86; H, 6.00; N, 16.09. Isomer B: 80 mg (MS). M. Pt.: Dec. 160° C. Calculated for C31H33N7O3.0.89 HCl: C, 63.75; H, 5.85; N, 16.79. Found: C, 63.76; H, 5.85; N, 16.70.

Provenance & Evidence