Reaktion #44633

Reaktionsgleichung

diisopropylazodicarboxylate

[(1R,2S)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester

4-nitrobenzoic acid

triphenylphosphine

→

title compound

Ausbeute 76.4%

4-nitrobenzoic acid (1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl ester

Ausbeute 76.4%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction solution
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   SonstigeThe residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3)
4. 4
   Sonstigethe obtained powder was triturated with toluene-hexane

Vorschrift

In nitrogen atmosphere, diisopropylazodicarboxylate (6 mL) was dropwise added under ice-cooling to a THF solution (100 mL) of [(1R,2S)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester (5.88 g), 4-nitrobenzoic acid (4.84 g), and triphenylphosphine (7.59 g). The resulting reaction solution was stirred at room temperature for 2 hr and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3), and then the obtained powder was triturated with toluene-hexane to give 6.69 g of the title compound. The physical property values of this compound were as follows:

Quelle