반응 #44638

반응 방정식

oxalyl chloride

water

methylene chloride

(S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol

→

title compound

(S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholin-2,3-dione

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타The resulting reaction solution
2. 2
   기타The organic layer was separated
3. 3
   세척washed with water, 1 N hydrochloric acid, water
4. 4
   건조Then, the organic layer was dried over anhydrous magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by silica gel column chromatography (heptane:ethyl acetate=9:1 to 3: 1)

실험 절차

In nitrogen atmosphere, oxalyl chloride (45 μL) was dropwise added under ice-cooling to a methylene chloride solution (2 mL) of (S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol (171 mg), TEA (0.17 mL), and 4-(N,N-dimethylamino)pyridine (8 mg). The resulting reaction solution was stirred at the same temperature for 2 hr, and then iced-water and ethyl acetate were added thereto. The organic layer was separated and washed with water, 1 N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution, and saturated saline in this order. Then, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=9:1 to 3: 1) to give 96 mg of the title compound. The physical property values of this compound were as follows:

출처