반응 #1771997

반응 방정식

Fmoc-norvaline

thionyl chloride

methanol

→

Fmoc-norVal-OMe

용매

ethylacetate

반응 조건

후처리

1. 1
   기타the completion of the reaction (Rf=0.85)
2. 2
   농축The reaction mixture was concentrated
3. 3
   workup.DISSOLUTIONthe remaining residue was dissolved in ethylacetate
4. 4
   세척The organic layer was washed with several 200 ml portions of saturated sodium bicarbonate
5. 5
   기타The organic layer was dried
6. 6
   여과filtered
7. 7
   농축concentrated

실험 절차

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).

출처