Sodium chloride dihydrate → 2-[[(5R)-2-oxo-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione

HRID 2188242Notes

Reaction equation

HRID 2188242 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[Cl-].[Na+].[OH2:15].[OH2:16]>CN(C=O)C>[O:15]=[C:1]1[NH:5][CH2:4][C@H:3]([CH2:2][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[O:16]1

Participants

4

Reactant 2

HCID 23713072Sodium chloride dihydrateHCID 24194345Phthalimide potassium salt

Product 1

HCID 116659572-[[(5R)-2-oxo-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of Example IA (22.16 g) in DMF (163 mL) at room temperature was treated with potassium phthalimide (16.7 g), heated to 80° C., stirred for 5 hours, poured into 1:1 brine/water (200 mL), and extracted with dichloromethane. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was treated with ethyl acetate (200 mL), cooled to 5° C., and filtered. The mother liquor was concentrated, treated with ethyl acetate (100 mL), cooled to 5° C., filtered, and combined with the first crop to provide the desired product. MS (ESI(+)) m/e 247 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.88 (m, 2H), 7.75 (m, 2H), 4.98 (m, 1H), 4.10 (dd, 1H), 3.90 (dd, 1H), 3.73 (t, 1H), 3.49 (dd, 1H).

Workup

  1. customat room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe concentrate was treated with ethyl acetate (200 mL)
  7. temperaturecooled to 5° C.
  8. filtrationfiltered
  9. concentrationThe mother liquor was concentrated
  10. additiontreated with ethyl acetate (100 mL)
  11. temperaturecooled to 5° C.
  12. filtrationfiltered

Sources & evidence

ORD record
ord-7a7b3dc171ee495fbf96a7cb03fc458b
Source dataset
uspto-grants-2002_06
Patent number
US06410728B1

Reaction notes

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