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Questions And Answer

• Synthesis

  Dimethylsulfoxide (1.25 mL, 17.6 mmol) was added to a solution of 2,4,6-trichloro- [1,3,5]-triazine (TCT, 0.66 g, 3.6 mmol) in THF (20 mL), stirred, and maintained at −30 °C. After 30 min, N-benzyloxycarbonyl-2-amino-3-phenylpropan-1-ol, (0.86 g, 3 mmol) in THF (10 mL) was added slowly at −30 °C with stirring, and after an additional 30 min, NEt3 (2 mL, 14.3 mmol) was added. After 15 min, the mixture was warmed to room temperature, the solvent evaporated in vacuo, and Et2O (50 mL) added to the resulting solid. The mixture was quenched with 1 N HCl, and the organic phase washed with 15 mL of a saturated solution of NaHCO3, followed by brine. The organic layer was dried (Na2SO4) and the solvent evaporated to yield pure N-benzyloxycarbonyl-2-amino-3-phenylpropionaldehyde (0.77 g, 90%).
  
  Reference: De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2001, 66, 7907−7909.;

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