反応 #433513

反応方程式

N-acetyl-3,5-dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio) -α-carbethoxy-phenylalanine ethyl ester

boron tribromide

→

4-(4'-Hydroxy-3'-(6-oxo-3(1H)-pyridylmethyl) phenylthio)-3,5-dichlorophenylalanine

収率 101.6%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred
2. 2
   workup.STIRRINGstirred for 5 hours
3. 3
   温度refluxed
4. 4
   濃縮with concentrated hydrochloric in glacial acetic acid in a manner similar to

実験手順

To a cooled (-74°) solution of N-acetyl-3,5-dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio) -α-carbethoxy-phenylalanine ethyl ester (0.39 g) in dry dichloromethane (10 ml) was added boron tribromide (0.58 ml) with stirring. The mixture was stirred whilst warming to room temperature and stirred for 5 hours. The reaction mixture was worked up and refluxed with concentrated hydrochloric in glacial acetic acid in a manner similar to that as described in Example 1 to afford DL-4-(4'-Hydroxy-3'-(6-oxo-3(1H)-pyridylmethyl) phenylthio)-3,5-dichlorophenylalanine as a cream solid (0.29 g, 70%), m.p. 261-264°.

出典