Sodium Hydroxide → HCID 90386740, compound

HRID 2170219Notes

Reaction equation

HRID 2170219 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[CH3:7][C:8]1[NH:9][C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[OH-].[Na+]>CN(C)C=O>[CH:2]([C:11]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([CH3:7])[NH:9][C:10]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 90387057HCID 90387057, compound

Product 1

HCID 90386740HCID 90386740, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Oxalyl dichloride (0.053 mL, 0.625 mmol) was added dropwise to N,N-dimethylformamide (0.387 mL, 5 mmol) at 0° C. The reaction mixture was removed from the cooling bath and stirred for thirty minutes at ambient temperature. N,N-Dimethylformamide (1 mL) was added to the reaction mixture and stirring was continued for another 30 minutes. The mixture was again cooled to 0° C. and a solution of Example 72b (0.161 g, 0.5 mmol) in N,N-dimethylformamide (2 mL) was added. Stirring was continued at 0° C. for two hours and then at ambient temperature for 3.5 hours. A solution of sodium hydroxide (10 mL, 4 N aqueous) was added and the mixture was stirred for 20 minutes. The reaction mixture was then partitioned between ethyl acetate and water, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 5-50% ethyl acetate in hexanes) to give 0.16 g (92%) of the title compound.

Workup

  1. customThe reaction mixture was removed from the cooling bath
  2. additionN,N-Dimethylformamide (1 mL) was added to the reaction mixture
  3. stirringstirring
  4. temperatureThe mixture was again cooled to 0° C.
  5. stirringStirring
  6. waitwas continued at 0° C. for two hours
  7. waitat ambient temperature for 3.5 hours
  8. stirringthe mixture was stirred for 20 minutes
  9. customThe reaction mixture was then partitioned between ethyl acetate and water
  10. washwashed with water and saturated aqueous sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe residue was purified by flash chromatography (silica gel, 5-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2ce525607e9f43dba0ff29988bba5d61
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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