Reaction #1624

Reaction equation

4-(2-t-Butoxycarbonylaminoethyl)phenoxymethylphosphonic acid, diethyl ester

→

title compound

4-(2-Aminoethyl)phenoxymethylphosphonic acid, diethyl ester

Solvents

methylene chloride

trifluoracetic acid

Conditions

Workup

1. 1
   ConcentrationThe solution was concentrated under reduced pressure and product
2. 2
   Otherdried under in vacuo
3. 3
   Extractionextracted with dichloromethane containing a small proportion of methanol (5×100 ml)
4. 4
   DryingThe combined organic layers were dried over sodium sulfate
5. 5
   Otherevaporated to dryness

Procedure

4-(2-t-Butoxycarbonylaminoethyl)phenoxymethylphosphonic acid, diethyl ester (2.856 g, 9.95 mMol) in methylene chloride (300 ml) and trifluoracetic acid (16 ml) was stirred at room temperature for 5 h. The solution was concentrated under reduced pressure and product dried under in vacuo. The trifluoacetic acid salt was neutralized with aqueous sodium carbonate and extracted with dichloromethane containing a small proportion of methanol (5×100 ml). The combined organic layers were dried over sodium sulfate and evaporated to dryness to give the title compound as a pale yellow gum.

Source