Sodium Hydroxide → HCID 22351125, compound

HRID 896500Notes

Reaction equation

HRID 896500 reaction equation
[N:1]1([CH2:10][CH2:11][O:12][C:13]2[CH:28]=[CH:27][C:16]([CH2:17][CH:18]([C:23]([O:25]C)=[O:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[OH-].[Na+]>CO.C1COCC1>[CH3:22][O:21][C:19](=[O:20])[CH:18]([CH2:17][C:16]1[CH:27]=[CH:28][C:13]([O:12][CH2:11][CH2:10][N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)=[CH:14][CH:15]=1)[C:23]([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10293251HCID 10293251, compound

Product 1

HCID 22351125HCID 22351125, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The compound obtained in Example 30 is dissolved in 5 ml of methanol and 3 ml of THF. The mixture is cooled to 0° C. and 0.44 ml of a 2M sodium hydroxide solution is added dropwise. After stirring for 1 hour 30 minutes at ambient temperature, the solvents are removed by evaporation under reduced pressure and the resulting residue is taken up in water and extracted with ethyl acetate. The aqueous phase is acidified with a 2M hydrochloric acid solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered, and evaporated under reduced pressure. The resulting residue is taken up in a minimum of ethyl acetate and precipitated with pentane to yield the title product after filtration.

Workup

  1. customthe solvents are removed by evaporation under reduced pressure
  2. extractionextracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customprecipitated with pentane

Sources & evidence

ORD record
ord-7494f43c35ca4de8adaef7037c6180de
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Reaction notes

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