Реакция #1771997

Уравнение реакции

Fmoc-norvaline

thionyl chloride

methanol

→

Fmoc-norVal-OMe

Растворители

ethylacetate

Условия реакции

Обработка

1. 1
   Другоеthe completion of the reaction (Rf=0.85)
2. 2
   КонцентрированиеThe reaction mixture was concentrated
3. 3
   workup.DISSOLUTIONthe remaining residue was dissolved in ethylacetate
4. 4
   ПромывкаThe organic layer was washed with several 200 ml portions of saturated sodium bicarbonate
5. 5
   ДругоеThe organic layer was dried
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated

Методика

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).

Источник