Reaktion #53962

Reaktionsgleichung

(2S,3S)-2-((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

→

(2S,3S)-3-hydroxy-2-((1S)-2-hydroxy-1-phenyl-ethylamino)-4-methyl-pentanoic acid tert-butyl ester

Ausbeute 55.0%

Lösungsmittel

tetrahydrofuran water formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe volatile was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in aqueous sodium bicarbonate solution
3. 3
   ExtraktionThe aqueous layer was extracted with ethyl acetate (3 times)
4. 4
   Waschenwashed with saturated sodium chloride solution
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=90:2:10)

Vorschrift

A solution of (2S,3S)-2-((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester (600 mg, 1.196 mmole, obtained from Reference Example 11) in a mixture of tetrahydrofuran : water: formic acid (3:1:1) was stirred at room temperature for 20 h. The volatile was removed in vacuo, and the residue was dissolved in aqueous sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate (3 times), and the extracts were combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=90:2:10) to give (2S,3S)-3-hydroxy-2-((1S)-2-hydroxy-1-phenyl-ethylamino)-4-methyl-pentanoic acid tert-butyl ester as a white solid (211 mg, 55%).

Quelle