Реакция #44638

Уравнение реакции

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

Растворители

ethyl acetate

Условия реакции

Обработка

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

Методика

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:

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