Sodium Hydroxide → HCID 18172495, compound

HRID 849291Notes

Reaction equation

HRID 849291 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]([O:13]CC)=[O:12])=[CH:7][N:6]=[CH:5]1)[CH:2]=[CH2:3].[OH-].[Na+]>CO.O>[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]([OH:13])=[O:12])=[CH:7][N:6]=[CH:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18172515HCID 18172515, compound

Product 1

HCID 18172495HCID 18172495, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To the compound of Example 21 (5.00 g, 0.024 mole), suspended in methanol (25 mL) and cooled in an ice bath, 1.0N NaOH (29 mL, 0.029 mole) is added dropwise rapidly with stirring. After 16 hours, the solvent is reduced under vacuum, residue diluted with water (50 mL), and washed with ethyl acetate (2×15 mL). The aqueous layer is acidified with 2.0N HCl to pH 1, extracted with ethyl acetate (3×50 mL). The combined organic extracts are washed with water, then brine (twice). The solvent is removed in vacuo to afford the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with ethyl acetate (2×15 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts are washed with water
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-699c2804a939452ab9bf2b6a6d739e2d
Source dataset
uspto-grants-2000_01
Patent number
US06011158

Reaction notes

Loading…