反应 #1771997

反应方程式

Fmoc-norvaline

thionyl chloride

methanol

→

Fmoc-norVal-OMe

溶剂

ethylacetate

反应条件

后处理

1. 1
   其他the completion of the reaction (Rf=0.85)
2. 2
   浓缩The reaction mixture was concentrated
3. 3
   workup.DISSOLUTIONthe remaining residue was dissolved in ethylacetate
4. 4
   洗涤The organic layer was washed with several 200 ml portions of saturated sodium bicarbonate
5. 5
   其他The organic layer was dried
6. 6
   过滤filtered
7. 7
   浓缩concentrated

实验过程

To a chilled solution of the commercially available Fmoc-norvaline (25 g, 73.75 mmol) in anhydrous methanol (469 ml) was added thionyl chloride (53.76 ml, 737.5 mmol) over one hour. TLC in ethylacetate taken an hour later confirmed the completion of the reaction (Rf=0.85). The reaction mixture was concentrated and the remaining residue was dissolved in ethylacetate. The organic layer was washed with several 200 ml portions of saturated sodium bicarbonate followed by brine. The organic layer was dried, filtered and concentrated to afford Fmoc-norVal-OMe) as a white solid (26.03 g) in quantitative yield. NMR δ ppm (CD3OD): 7.7 (m, 2H), 7.6 (m, 2H), 7.4 (m, 2H), 7.3 (m, 2H), 4.3 (m, 2H), 4.1 (m, 2H), 3.7 (s, 3H), 1.7 (m, 1H), 1.6 (m, 1H), 1.4 (m, 2H), 0.95 (t, 3H).

来源