반응 #1416

반응 방정식

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

용매

—

hexanes

ethyl acetate

ethyl acetate

반응 조건

후처리

1. 1
   기타the residual water removed azeotropically with acetonitrile (3×)
2. 2
   기타The resulting oil was dried in vacuo
3. 3
   workup.DISSOLUTIONdissolved in dry dimethyl-formamide
4. 4
   세척washed successively with water (2×25 ml.), saturated sodium bicarbonate (25 ml.) and brine (25 ml.)
5. 5
   건조The organic phase was dried (anhydrous magnesium sulfate)
6. 6
   여과filtered
7. 7
   기타evaporated to dryness
8. 8
   기타dried in vacuo
9. 9
   기타to give 10.11 g

실험 절차

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).

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