Lithium Hydroxide → HCID 59430834, compound

HRID 505687Notes

Reaction equation

HRID 505687 reaction equation
[CH3:1][C@@H:2]([O:11][CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:35]=[CH:34][C:18]([CH2:19][N:20]2[CH:24]=[CH:23][CH:22]=[C:21]2[C:25]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)=[O:26])=[CH:17][CH:16]=1)[C:3](N1CCOCC1)=[O:4].C1C[O:39]CC1.[OH-].[Li+]>CO.O>[CH3:33][C:30]1[CH:29]=[CH:28][C:27]([C:25]([C:21]2[N:20]([CH2:19][C:18]3[CH:34]=[CH:35][C:15](/[CH:14]=[CH:13]/[CH2:12][O:11][C@H:2]([CH3:1])[C:3]([OH:4])=[O:39])=[CH:16][CH:17]=3)[CH:24]=[CH:23][CH:22]=2)=[O:26])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59430823HCID 59430823, compound

Product 1

HCID 59430834HCID 59430834, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound of Example 68-1 (213 mg, 0.45 mmol) was dissolved in methanol (1 ml) and THF (1 ml) and thereto was added 2N aqueous lithium hydroxide (0.9 ml), followed by stirring under reflux for 7 hours. The reaction mixture was diluted with water and washed with diethyl water. 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 (155 mg, 85%).

Workup

  1. temperatureunder reflux for 7 hours
  2. washwashed with diethyl water
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e34c220caa15406e9f101f8c30bb2fd2
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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