Reaction #89729

Reaction equation

pyridinium p-toluenesulfonate

1-benzyl 4-methyl(2S)-2-[benzyl((2R)-2-hydroxy-3-[(4-methylphenyl)sulfonyl]oxypropyl)amino]succinate

methylene chloride

ethyl vinyl ether

→

1-benzyl 4-methyl(2S)-2-[benzyl((2R)-2-(1-ethoxyethoxy)-3-[(4-methylphenyl)sulfonyl]oxypropyl)amino]succinate

Conditions

Workup

1. 1
   ConcentrationAfter concentrated
2. 2
   Otherto dry
3. 3
   Otherthe residue was purified by silical gel column (eluting with 0 to 20% EtOAc in hexane)
4. 4
   Otherto provide the ether compound (38.1 g, 78.4%)

Procedure

To a solution of 1-benzyl 4-methyl(2S)-2-[benzyl((2R)-2-hydroxy-3-[(4-methylphenyl)sulfonyl]oxypropyl)amino]succinate (43.0 g, 0.0774 mol) in methylene chloride (500.0 mL, 7.800 mol) was added ethyl vinyl ether (15.0 mL, 0.157 mol) followed by pyridinium p-toluenesulfonate (4.0 g, 0.016 mol). The mixture was stirred at rt for 3 g. After concentrated to dry, the residue was purified by silical gel column (eluting with 0 to 20% EtOAc in hexane) to provide the ether compound (38.1 g, 78.4%). MS (ESI): (M+H)+=628.1.

Source