Reaction #577254

Reaction equation

(R)-4-(di-tert-butoxy-phosphoryloxymethyl)-4-(2-{4-[2-(3-fluoro-phenoxy)-ethoxy]-phenyl}-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

→

phosphoric acid mono-((R)-2-amino-4-{4-[2-(3-fluoro-phenoxy)-ethoxy]-phenyl}-2-hydroxymethyl-butyl)ester

Solvents

HCl

Conditions

Workup

1. 1
   Temperatureis then heated to 95° C. for 2 hours
2. 2
   Concentrationconcentrated to dryness
3. 3
   workup.DISSOLUTIONThe residue is re-dissolved in ethyl acetate
4. 4
   Otherprecipitated with hexanes
5. 5
   FiltrationThe solid is filtered off
6. 6
   Washwashed with dry ether
7. 7
   Otherdried in vacuo

Procedure

Finally, a solution of (R)-4-(di-tert-butoxy-phosphoryloxymethyl)-4-(2-{4-[2-(3-fluoro-phenoxy)-ethoxy]-phenyl}-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (70 mg, 0.10 mmol) in conc. HCl (2 ml). is stirred at room temperature for one hour and is then heated to 95° C. for 2 hours, then concentrated to dryness. The residue is re-dissolved in ethyl acetate and precipitated with hexanes. The solid is filtered off, washed with dry ether and dried in vacuo to afford phosphoric acid mono-((R)-2-amino-4-{4-[2-(3-fluoro-phenoxy)-ethoxy]-phenyl}-2-hydroxymethyl-butyl)ester as a colorless powder.

Source