反応 #41267

反応方程式

hydroxylamine hydrochloride

HATU

DIPEA

E-3-chloro-4-hydroxyphenylcinnamic acid

→

title compound

収率 9.7%

E-3-[3′-chloro-4′-hydroxybiphenyl-4-yl]-N-hydroxy-acrylamide

収率 9.7%

溶媒

DMF

反応条件

後処理

1. 1
   その他the solution thus obtained
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 2 days
3. 3
   その他DMF was removed under reduced pressure
4. 4
   洗浄the residue was washed with water
5. 5
   その他to obtain
6. 6
   ろ過after filtration, 140 mg of a crude product
7. 7
   その他Purification by flash chromatography on reverse phase ((LiChroprep RP-18, MERCK)
8. 8
   その他water/methanol 1:1 and crystallization from diethyl ether

実験手順

205 mg (0.75 mmol) of E-3-chloro-4-hydroxyphenylcinnamic acid were dissolved under nitrogen in 7.5 ml of DMF, then 285 mg (0.75 mmol) of HATU and 97 μL (0.56 mmol) of DIPEA were added and the solution thus obtained was kept under stirring at room temperature for 2 min. After addition of hydroxylamine hydrochloride (261 mg, 3.75 mmol), the mixture was stirred at room temperature for 2 days. DMF was removed under reduced pressure and the residue was washed with water to obtain, after filtration, 140 mg of a crude product. Purification by flash chromatography on reverse phase ((LiChroprep RP-18, MERCK) using as eluent water/methanol 1:1 and crystallization from diethyl ether afforded 21 mg of the title compound as a white solid. M.p. 172-175° C. Rf=0.16 (RP18 MERCK, H2O/MeOH 1:1).

出典