Reaction #586112

Reaction equation

methyl 5-benzyloxy-2-hydroxybenzoate

2-(S)-amino-3-phenyl-1-propanol

→

N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide

Yield 50.0%

Solvents

dimethyl formamide

ethyl acetate

hexane

Conditions

Workup

1. 1
   OtherIn a flask equipped with a reflux condenser and a magnetic stirring bar
2. 2
   OtherThe flask is immersed in an oil bath at 75° C.
3. 3
   workup.WAITleft
4. 4
   OtherThe solvent is evaporated
5. 5
   Otherthe residue is isolated-through the use of a silica gel column

Procedure

In a flask equipped with a reflux condenser and a magnetic stirring bar are dissolved the methyl 5-benzyloxy-2-hydroxybenzoate and one equivalent of 2-(S)-amino-3-phenyl-1-propanol in dry dimethyl formamide. The flask is immersed in an oil bath at 75° C. and left to stir for 72 hours. The solvent is evaporated and the residue is isolated-through the use of a silica gel column using a mixture of ethyl acetate and hexane as eluent. In this fashion is obtained in 50% yield, N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide.

Source