反应 #1375810

反应方程式

hydrochloric acid

tyrosine-tert-butyl ester

benzaldehyde

sodium bicarbonate

sodium cyanoborohydride

→

N-Benzyl-tyrosine-tert-butyl ester

溶剂

methanol

反应条件

后处理

1. 1
   其他after substantial evaporation of methanol, it
2. 2
   workup.STIRRINGis shaken out with ethyl acetate
3. 3
   干燥The organic phase is dried on anhydrous magnesium sulfate
4. 4
   过滤filtered
5. 5
   浓缩concentrated by evaporation
6. 6
   其他The residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine
7. 7
   浓缩concentrated by evaporation

实验过程

16.9 g (71.5 mmol) of tyrosine-tert-butyl ester and 8.33 g (78.6 mmol) of benzaldehyde are stirred in 50 ml of methanol for 3 hours at 24° C. and then mixed with 3.37 g (53.6 mmol) of sodium cyanoborohydride. After 24 hours of stirring at room temperature, the batch is adjusted to pH 2 by careful addition of semiconcentrated hydrochloric acid, then neutralized with concentrated aqueous sodium bicarbonate solution and, after substantial evaporation of methanol, it is shaken out with ethyl acetate. The organic phase is dried on anhydrous magnesium sulfate, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine; the product-containing fractions are combined and concentrated by evaporation.

来源