反应详情

Methyl O-(3′-amino-1,1′-biphenyl-3-yl)-N-triphenylmethyl-L-serinate (Example 2) (250.0 mg, 0.47 mmol, 1 equiv) was dissolved in toluene (5 mL) and treated at rt with n-propyl isocyanate (402.5 mg, 4.73 mmol, 10 equiv) and DABCO (1,4-diazabicyclo[2,2,2]octane) (5.3 mg, 0.05 mmol, 0.1 equiv). The reaction mixture was stirred at rt for 14 h and then partitioned between toluene and sat. aqueous NH4Cl solution. The organic layer was separated and dried over NaSO4 and the solvents were removed in vacuuo. The crude product was titurated with petroleum ether to give a yellow solid. Yield 210.0 mg, 72.4%. 1H NMR (CDCl3, 200 MHz) δ 7.65-7.50 (m, 9H); 7.40-7.15 (m, 12H); 6.95 (d, 2H); 5.19-4.98 (m, 1H); 4.25 (dd, 1H); 4.03 (dd, 1H); 3.38-3.02 (m, 4H); 2.88 (d, 1H); 1.65-1.45 (m, 2H); 0.90 (t, 3H). MS (EI) 614 (M+H), 243 (CPh3).

1. custompartitioned between toluene and sat. aqueous NH4Cl solution
2. customThe organic layer was separated
3. dry with materialdried over NaSO4
4. customthe solvents were removed in vacuuo
5. customto give a yellow solid