Reaction #44638

Reaction equation

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

Solvents

ethyl acetate

Conditions

Workup

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

Procedure

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:

Source