Reaktion #2075761

Reaktionsgleichung

(S)-glycidyl 3-nitrobenzenesulfonate

sodium hydride

4-(tert-butoxycarbonylamino)phenol

→

compound ( 9 )

Ausbeute 83.0%

(2S)-1-[4-(tert-butoxycarbonylamino)phenoxy]-2,3-epoxypropane

Ausbeute 83.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added, under ice cooling
2. 2
   SonstigeThe reaction was quenched with a 5 ml of saturated aqueous ammonium chloride solution
3. 3
   Extraktionthe product was extracted with ether
4. 4
   WaschenThe extract was washed with saturated saline
5. 5
   Sonstigedried
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   Sonstigeto give a residue, which
9. 9
   Sonstigewas then purified by silica gel column.chromatography (hexane:ethyl acetate=3:1)

Vorschrift

To an 8 ml dimethylformamide suspension of 60 mg of sodium hydride was added, under ice cooling, 300 mg of 4-(tert-butoxycarbonylamino)phenol. The resultant mixture was stirred at room temperature for 1 hour. Under ice cooling, 372 mg of (S)-glycidyl 3-nitrobenzenesulfonate was gradually added, then the resultant mixture was stirred at room temperature for 2 hours. The reaction was quenched with a 5 ml of saturated aqueous ammonium chloride solution, then the product was extracted with ether. The extract was washed with saturated saline, dried, filtered, then concentrated under reduced pressure to give a residue, which was then purified by silica gel column.chromatography (hexane:ethyl acetate=3:1) to give the above-referenced compound (9) in an amount of 315 mg (yield 83%).

Quelle