Sodium Hydroxide → HCID 18172495, compound

HRID 2257102Notes

Reaction equation

HRID 2257102 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-15f76a781d22480eb80aad261d1b5b81
Source dataset
uspto-grants-1997_08
Patent number
US05656645

Reaction notes

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