反応 #44610

反応方程式

oxalyl chloride

methylene chloride

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

water

→

title compound

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

溶媒

ethyl acetate

反応条件

後処理

1. 1
   温度cooling
2. 2
   温度cooling for 2 hr
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with water, 1 N hydrochloric acid, water
5. 5
   乾燥Then, the organic layer was dried over anhydrous magnesium sulfate
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residue was purified by silica gel column chromatography (eluting solvent; heptane:ethyl acetate=9:1 to 3:1)

実験手順

In nitrogen atmosphere, oxalyl chloride (45 μL) was dropwise added 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) under ice-cooling. This reaction solution was stirred under ice-cooling for 2 hr. To the reaction solution, iced-water and ethyl acetate were added. The organic layer was separated, 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 (eluting solvent; 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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