Lithium Hydroxide → HCID 59430835, compound

HRID 505688Notes

Reaction equation

HRID 505688 reaction equation
[CH3:1][C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[CH2:20][O:21][C@H:22]([CH3:31])[C:23](N3CCOCC3)=[O:24])=[CH:14][CH:13]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:32]([C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1)=[O:33].C1C[O:44]CC1.[OH-].[Li+]>CO.O>[CH3:1][C:2]1[N:10]([CH2:11][C:12]2[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[CH2:20][O:21][C@H:22]([CH3:31])[C:23]([OH:44])=[O:24])=[CH:16][CH:17]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:32](=[O:33])[C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59430803HCID 59430803, compound

Product 1

HCID 59430835HCID 59430835, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound of Example 74-1 (33 mg, 0.06 mmol) was dissolved in methanol (1 ml) and THF (1 ml) and thereto was added 2N aqueous lithium hydroxide solution (1 ml), followed by stirring under reflux for 8 hours. The mixture was diluted with water and washed with ethyl ether. The aqueous layer was adjusted to around pH 4 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 (28 mg, 96%).

Workup

  1. temperatureunder reflux for 8 hours
  2. washwashed with ethyl ether
  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-30713d5bcedf471aa4aa2328ed8a4857
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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