反応 #1771997

反応方程式

Fmoc-norvaline

thionyl chloride

methanol

→

Fmoc-norVal-OMe

溶媒

ethylacetate

反応条件

後処理

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

実験手順

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).

出典