反应 #3873

反应方程式

diazomethane

dry ice acetone

N-p-methoxybenzyloxycarbonyl-D-serine benzyl ester

Boron trifluoride etherate

→

title compound

收率 70.0%

N-p-Methoxybenzyloxycarbonyl-O-methyl-D-serine benzyl ester

收率 70.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   过滤After about 30 minutes the solution is filtered
2. 2
   洗涤washed once with water (10 ml)
3. 3
   干燥dried (MgSO4)
4. 4
   其他evaporated to dryness
5. 5
   其他The resulting residue is chromatographed on silica gel

实验过程

The N-p-methoxybenzyloxycarbonyl-D-serine benzyl ester (720 mg, 2.00 mmol) is dissolved in dry dichloromethane (20 ml) and the solution cooled to dry ice/acetone. Boron trifluoride etherate (100 μl) is added followed by the portionwise addition of diazomethane (30 mmol in 20 ml CH2Cl2). After about 30 minutes the solution is filtered and washed once with water (10 ml), then dried (MgSO4) and evaporated to dryness. The resulting residue is chromatographed on silica gel using chloroform as eluant to give the pure title compound as an oil (520 mg, 70%) which crystallises on standing to give a colourless solid of m.p. 68°-69° C.; [α]D20 -1.3° (c 4.0, CHCl3).

来源