Reaction #577240

Reaction equation

HCl

(R/S)-FTY720-phosphate

Phosphoric acid mono-[(R/S)-2-amino-2-hydroxymethyl-4-(4-octyl-phenyl)-butyl]ester

EDTA

boric acid

→

Phosphoric acid mono-[(R/S)-2-hydroxymethyl-4-(4-octyl-phenyl)-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-butyl]ester

Solvents

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONAfter addition of OPA (33 mg, 0.25 mmol)
2. 2
   Extractionextracted with ethylacetate (three times)
3. 3
   DryingThe organic layer is dried over Na2SO4
4. 4
   Otherthe compound is purified on silica gel

Procedure

The endproduct of step d) ((R/S)-FTY720-phosphate) (50 mg; 0.125 mmol) is suspended in a solution of EDTA (0.5 ml; 10 mM in water) and aqueous boric acid (0.5 ml; 3% in water; adjusted to pH 10.5 with aqueous KOH10%). After addition of OPA (33 mg, 0.25 mmol), dissolved in ethanol (0.5 ml), the reaction is kept at RT for 1 hour (ultrasound). After that the pH is adjusted to 3.5 (aqueous HCl; 1N) and extracted with ethylacetate (three times). The organic layer is dried over Na2SO4 and the compound is purified on silica gel using methylenechloride/methanol (95/5→0/100) as mobile phase.

Source