Sodium Hydroxide → HCID 72188729, compound

HRID 1486598Notes

Reaction equation

HRID 1486598 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:20])/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:4].[OH-].[Na+]>CO>[C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])(=[O:20])/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 72188730HCID 72188730, compound

Product 1

HCID 72188729HCID 72188729, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 3 (0.84 g, 3 mmol) was dissolved in methanol (40 mL), and a 1 mol/L aqueous sodium hydroxide solution (4 mL, NaOH 4 mmol) was added thereto at room temperature, and the mixture was stirred for 20 hours. The solvent was distilled off under a reduced pressure, and the residue was then dissolved in water, and a 10% aqueous citric acid solution was added thereto to adjust its pH to about 4. The liquid mixture was extracted with dichloromethane, an organic layer was washed with water and saturated sodium chloride solution, and the washed extract was then dried over anhydrous sodium sulfate, to give an intended compound (0.72 g, 90%) in the form of a colorless oily substance.

Workup

  1. distillationThe solvent was distilled off under a reduced pressure
  2. dissolutionthe residue was then dissolved in water
  3. additiona 10% aqueous citric acid solution was added
  4. extractionThe liquid mixture was extracted with dichloromethane
  5. washan organic layer was washed with water and saturated sodium chloride solution
  6. extractionthe washed extract
  7. dry with materialwas then dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-2892a9eab30e4422a37a537d16303cbf
Source dataset
uspto-grants-2016_08
Patent number
US09428477B2

Reaction notes

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