Lithium Hydroxide → HCID 59430962, compound

HRID 505684Notes

Reaction equation

HRID 505684 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][C@H:21]([CH3:30])[C:22](N3CCOCC3)=[O:23])=[CH:15][CH:14]=1)[C:7]([CH3:31])=[C:6]2[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][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][C@H:21]([CH3:30])[C:22]([OH:23])=[O:44])=[CH:15][CH:14]=1)[C:7]([CH3:31])=[C:6]2[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 59430919HCID 59430919, compound

Product 1

HCID 59430962HCID 59430962, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound of Example 40-1 (142 mg, 0.26 mmol) was dissolved in methanol (1 ml) and THF (1 ml) and thereto was added 2N lithium hydroxide solution (0.5 ml), followed by stirring under reflux for 15 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 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 (39 mg, 31%).

Workup

  1. temperatureunder reflux for 15 hours
  2. washwashed with diethyl ether
  3. extractionextracted 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-c88a73c558d64b5ca9a80057be90c227
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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