Sodium Carbonate → HCID 66666133, compound

HRID 81589Notes

Reaction equation

HRID 81589 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C:8]2([CH2:15]O)[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:7]=1.C(N(S(F)(F)[F:24])CC)C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C:8]2([CH2:15][F:24])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 66665931HCID 66665931, compound

Product 1

HCID 66666133HCID 66666133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-bromo-2-fluoro-phenyl)-5-hydroxymethyl-morpholin-3-one (1.6 g, 5.26 mmol) in 30 ml THF was added dropwise diethylaminosulfur trifluoride (0.97 ml, 7.34 mmol) and stirred for 2 h. The colorless solution was slowly added to an ice cooled Na2CO3 solution (10%, aqueous) and extracted with TBME. The organic layer was washed with brine, dried with MgSO4 and evaporated. The crude product was purified by chromatography on silica gel (heptane/EtOAc 3/1) to provide the title compound as a slightly yellow solid.

Workup

  1. extractionextracted with TBME
  2. washThe organic layer was washed with brine
  3. dry with materialdried with MgSO4
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica gel (heptane/EtOAc 3/1)

Sources & evidence

ORD record
ord-c34bcbfc91db4914838a70e9a11ab68c
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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