Reaction #89716

Reaction equation

pyridinium p-toluenesulfonate

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

methylene chloride

ethyl vinyl ether

→

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

Conditions

Workup

1. 1
   Concentrationconcentrated
2. 2
   Otherto dry
3. 3
   Otherpurified on silical gel (eluting with 0 to 20% EtOAc in hexane)
4. 4
   Otherto afford the ether compound (39.7 g, 81.7%)

Procedure

To a mixture of 1-benzyl 4-methyl(2S)-2-[benzyl((2S)-2-hydroxy-3-[(4-methylphenyl)sulfonyl]oxypropyl)amino]succinate (43.0 g, 0.0774 mol) in methylene chloride (600.0 mL, 9.360 mol) was added ethyl vinyl ether (14.8 mL, 0.155 mol) followed by pyridinium p-toluenesulfonate (1 g, 0.004 mol). The mixture was stirred at rt for 1 h, concentrated to dry and purified on silical gel (eluting with 0 to 20% EtOAc in hexane) to afford the ether compound (39.7 g, 81.7%). MS (ESI): (M+H)+=628.1.

Source