Tetrahydrofuran → HCID 59430970, compound

HRID 505686Notes

Reaction equation

HRID 505686 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:30](=[O:38])[C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)=[C:8]([CH3:29])[N:9]2[CH2:12][C:13]2[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=2)[CH2:16][O:17][C:18]2([C:21]([O:23]CC)=[O:22])[CH2:20][CH2:19]2)=[CH:5][CH:4]=1.C1COCC1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:30](=[O:38])[C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)=[C:8]([CH3:29])[N:9]2[CH2:12][C:13]2[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=2)[CH2:16][O:17][C:18]2([C:21]([OH:23])=[O:22])[CH2:19][CH2:20]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59430767HCID 59430767, compound

Product 1

HCID 59430970HCID 59430970, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound of Example 66-1 (10 mg, 0.02 mmol) was dissolved in methanol (1 ml) and THF (1 ml) and thereto was added 1N aqueous sodium hydroxide solution (1 ml), followed by stirring for 20 hours. The reaction mixture was diluted with water and washed with diethyl ether. The aqueous layer was adjusted to around pH4 with 5% aqueous potassium hydrogen sulfate solution and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo to give the subject compound (quant.).

Workup

  1. washwashed with diethyl ether
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customto give the subject compound (quant.)

Sources & evidence

ORD record
ord-2bbb9f9ccdd34288aba93a6e682cab44
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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