反应 #1416

反应方程式

methyl iodide

Cesium carbonate

N2 [(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine

water methanol

→

N2 [(1,1-Dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine, methyl ester

溶剂

—

hexanes

ethyl acetate

ethyl acetate

反应条件

后处理

1. 1
   其他the residual water removed azeotropically with acetonitrile (3×)
2. 2
   其他The resulting oil was dried in vacuo
3. 3
   workup.DISSOLUTIONdissolved in dry dimethyl-formamide
4. 4
   洗涤washed successively with water (2×25 ml.), saturated sodium bicarbonate (25 ml.) and brine (25 ml.)
5. 5
   干燥The organic phase was dried (anhydrous magnesium sulfate)
6. 6
   过滤filtered
7. 7
   其他evaporated to dryness
8. 8
   其他dried in vacuo
9. 9
   其他to give 10.11 g

实验过程

Cesium carbonate (4.28 g., 13.1 moles) was added to a mixture of N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (10 g., 26.3 moles) and 20% water-methanol (60 ml.). The solution became homogeneous within 5 minutes so the solvent was stripped and the residual water removed azeotropically with acetonitrile (3×). The resulting oil was dried in vacuo, dissolved in dry dimethyl-formamide and treated with methyl iodide (3.2 ml., 2.0 eq.). The reaction mixture was stirred at room temperature for 1.5 hours under argon, diluted with ethyl acetate (200 ml.) and washed successively with water (2×25 ml.), saturated sodium bicarbonate (25 ml.) and brine (25 ml.). The organic phase was dried (anhydrous magnesium sulfate), filtered, evaporated to dryness and dried in vacuo to give 10.11 g., of product as a light yellow syrup; Rf =0.30 (ethyl acetate:hexanes, 1:2).

来源