Methanol → HCID 59430737, compound

HRID 505681Notes

Reaction equation

HRID 505681 reaction equation
[CH3:1][C:2]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]\[CH2:18][N:19]2[CH:23]=[CH:22][CH:21]=[C:20]2[C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[CH:12][CH:11]=1)([CH3:7])[C:3]([O:5]C)=[O:4].CO.[OH-].[Li+]>C1COCC1.O>[CH3:7][C:2]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]\[CH2:18][N:19]2[CH:23]=[CH:22][CH:21]=[C:20]2[C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[CH:12][CH:11]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59430960HCID 59430960, compound

Product 1

HCID 59430737HCID 59430737, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the compound of Example 1-1 (410 mg, 0.95 mmol) in THF (4 ml) were added methanol (4 ml) and 1N aqueous lithium hydroxide solution (4 ml), followed by stirring for 8 hours at room temperature. The reaction mixture was diluted with water and washed with diethyl ether. To the aqueous layer was added 5% aqueous potassium hydrogen sulfate solution and the solution was adjusted around pH3 and extracted with ethyl acetate. The organic layer was washed with water, saturated brine, dried over magnesium sulfate and filtered. The solvent was removed in vacuo to give the subject compound (262 mg, 66%).

Workup

  1. washwashed with diethyl ether
  2. additionTo the aqueous layer was added 5% aqueous potassium hydrogen sulfate solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7ca2519b625243499d36f1665f32c060
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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