Sodium Hydroxide → HCID 10994373, compound

HRID 324588Notes

Reaction equation

HRID 324588 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:19]([C:20]([O:22]C)=[O:21])=[C:18]([C:24]4[CH:32]=[CH:31][C:27]5[O:28][CH2:29][O:30][C:26]=5[CH:25]=4)[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:33][CH:34]([CH3:36])[CH3:35])[CH:16]=4)[O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:19]([C:20]([OH:22])=[O:21])=[C:18]([C:24]4[CH:32]=[CH:31][C:27]5[O:28][CH2:29][O:30][C:26]=5[CH:25]=4)[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:33][CH:34]([CH3:36])[CH3:35])[CH:16]=4)[O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11730649HCID 11730649, compound

Product 1

HCID 10994373HCID 10994373, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound (Ia-3) (57 mg, 0.117 mmol) and 1 M aqueous solution of sodium hydroxide (1.2 ml) in THF (2 ml) and methanol (2 ml) were refluxed for 1 h. The solvent was removed under reduced pressure, acidified with hydrochloric acid and extracted with ether three times. The ether layers were combined, washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from acetone-isopropylether to give compound (I-1) (37 mg, 66%) as yellow crystals.

Workup

  1. temperaturewere refluxed for 1 h
  2. customThe solvent was removed under reduced pressure
  3. extractionextracted with ether three times
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from acetone-isopropylether
  8. customto give compound (I-1) (37 mg, 66%) as yellow crystals

Sources & evidence

ORD record
ord-cde4de7bab7f476cade382e8f0190c04
Source dataset
uspto-grants-2001_04
Patent number
US06218427B1

Reaction notes

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