A Convenient Synthesis of DI-(Benzyloxycarbonyl)-Protected Guanidines

Notes and References

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• Satisfactory spectral data were obtained for all products. Elemental analysis data: 3a, C25H25N3O4, Calc'd: C 69.58, H 5.84, N 9.73; Found: C 69.43, H 5.77, N 9.73; 3b, C25H23N3O6, Calc'd: C 65.06, H 5.02, N 9.10; Found: C 64.70, H 5.06, N 9.05; 3c, C23H18F3N3O4, Calc'd: C 60.40, H 3.94, N 9.18; Found: C 60.46, H 3.97, N 9.32; 3d, C21H25N3O4, Calc'd: C 65.77, H 6.57, N 10.95; Found: C 65.83, H 6.59, N 11.03; 3f, C26H33N3O4·½H2O, Calc'd: C 67.80, H 7.44, N 9.12; Found: C 67.71, H 7.24, N 9.18.
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• For 3a: 1H-NMR (250 MHz, CDCl3); δ 11.91, (s, 1H), 10.12 (s, 1H), 7.39–7.30, (m, 11H), 7.22 (d, J = 2.0 Hz, 1H), 7.1 (d, J = 8.1 Hz, 1H), 5.23 (s, 2H), 5.14 (s, 2H), 2.24 (s, 3H), 2.22 (s, 3H); MS (Cl, NH3); (m/z) 432 M+1).
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• For 4a: 1H-NMR (250 MHz, CDCl3-CD3OD): δ 6.99 (d, J = 8.23 Hz, 1H), 6.76 (d, J = 1.83 Hz, 1H), 6.70 (dd, J = 2.08, 8.09 Hz, 1H), 2.11 (s, 6H); MS (Cl, NH3): (m/z) 164 (M+1).
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