반응 #44602

반응 방정식

diisopropyl azodicarboxylate

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

4-nitrobenzoic acid

triphenylphosphine

→

title compound

수율 76.4%

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

수율 76.4%

용매

THF

반응 조건

후처리

1. 1
   온도cooling
2. 2
   농축concentrated under reduced pressure
3. 3
   기타The obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3)
4. 4
   기타to give a powder
5. 5
   기타The obtained powder was triturated with toluene-hexane

실험 절차

In nitrogen atmosphere, diisopropyl azodicarboxylate (6 mL) was dropwise added 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) under ice-cooling. This reaction solution was stirred at room temperature for 2 hr and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3) to give a powder. 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:

출처