反应 #1820424

反应方程式

L-arabinose

benzylamine

2-chloroethyl isocyanate

→

1-(2-chloroethyl)-3-benzyl-3-(L-arabinopyranosyl)urea

收率 90.0%

溶剂

methanol

formic acid

formic acid

tetrahydrofuran

methanol

反应条件

后处理

1. 1
   其他After the reaction
2. 2
   其他condensed to dryness under reduced pressure
3. 3
   洗涤the residue is washed with ether, whereby 4.7 g of 1-benzylamino-1-deoxy-L-arabinose
4. 4
   其他are obtained as a crude product
5. 5
   其他at 0° to 5° C
6. 6
   workup.STIRRINGThe solution is stirred at room temperature for one hour
7. 7
   其他condensed under reduced pressure
8. 8
   其他the residue thus obtained
9. 9
   其他The resultant oil is collected by decantation
10. 10
    洗涤washed with ether
11. 11
    其他purified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol (2:5:1))

实验过程

A mixture of 3.0 g of L-arabinose, 4.3 g of benzylamine and 10 ml of methanol is heated at 60° C. for one hour under stirring. After the reaction, the mixture is condensed to dryness under reduced pressure and the residue is washed with ether, whereby 4.7 g of 1-benzylamino-1-deoxy-L-arabinose are obtained as a crude product. 4.7 g of said crude product are dissolved in 30 ml of methanol, and a solution of 2.5 g of 2-chloroethyl isocyanate in 10 ml of tetrahydrofuran is added dropwise thereto at 0° to 5° C. The solution is stirred at room temperature for one hour. Then, the reaction solution is condensed under reduced pressure, and the residue thus obtained is dissolved in 15 ml of formic acid. The formic acid solution is allowed to stand at room temperature for 15 minutes, and 150 ml of ether-n-hexane (3:1) are added thereto. The resultant oil is collected by decantation, washed with ether and then purified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol (2:5:1)). 6.2 g of 1-(2-chloroethyl)-3-benzyl-3-(L-arabinopyranosyl)urea are thereby obtained as colorless caramel.

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