Diisopropylethylamine → (RS)-6-Phenyl-4-(7-phenyl-heptanoylamino)-hexanoic acid

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Reaction Steps

Phenylheptanoic acid (105 mg 0.51 mmol) and BOP (250 mg, 0.56 mmol) were dissolved in dry DMF 2 mL then DIPEA 200 μL was added. After mixing for 3 min the solution was added to (RS)-4-amino-6-phenyl-hexanoic acid (101) (105 mg, 0.51 mmol) and the solution was stirred at room temperature for 1 hr. Ether was added and the solution was washed twice with 1 M HCl and brine then dried over MgSO4. Removal of solvent gave a white solid 200 mg, which was recrystallised from EtOAc-hexane. 1H NMR (300 MHz, CDCl3) δ 7.30-7.22 (m, 4H), 7.21-7.11 (m, 6H), 6.17 (br, 1H, NH), 4.02 (m, 1H), 2.70-2.53 (m, 4H), 2.38 (m, 2H), 2.22 (m, 2H), 2.00-1.52 (m, 8H), 1.44-1.27 (m, 4H).

Provenance & Evidence