Lithium Hydroxide → HCID 59430749, compound

HRID 505690Notes

Reaction equation

HRID 505690 reaction equation
[CH3:1][C:2]1[N:3]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][O:27][C@H:28]([CH3:37])[C:29](N3CCOCC3)=[O:30])=[CH:22][CH:21]=2)[C:4]2[C:9]([C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.C1C[O:41]CC1.[OH-].[Li+]>CO.O>[CH3:1][C:2]1[N:3]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][O:27][C@H:28]([CH3:37])[C:29]([OH:41])=[O:30])=[CH:24][CH:25]=2)[C:4]2[C:9]([C:10]=1[C:11](=[O:12])[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59430854HCID 59430854, compound

Product 1

HCID 59430749HCID 59430749, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound of Example 89-1 (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 10 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 (quant.).

Workup

  1. temperatureunder reflux for 10 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
  8. customto give the subject compound (quant.)

Sources & evidence

ORD record
ord-2b08271f28bb40c38d8b3698e1213b31
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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