Lithium hydroxide, monohydrate → HCID 58790243, compound

HRID 418718Notes

Reaction equation

HRID 418718 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]([O:9]C)=[O:8])[CH2:5][CH2:4][N:3]1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.O[Li].O>C1COCC1.O>[O:1]=[C:2]1[CH:6]([C:7]([OH:9])=[O:8])[CH2:5][CH2:4][N:3]1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58790151HCID 58790151, compound

Product 1

HCID 58790243HCID 58790243, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 350 (514 mg, 2.33 mmol) in THF (20 ml) under nitrogen was added a solution of LiOH.H2O (147 mg, 3.50 mmol) in water (5 mL). The reaction mixture was stirred overnight, concentrated, diluted with a small amount of water, filtered, neutralized with 1N HCl (pH ˜5-6), and extracted twice with dichloromethane. The aqueous phase was concentrated, and the residue was triturated in methanol (with traces of acetone). After filtration, the mother liquid was concentrated and dried under high vacuum to afford title compound 351 (493 mg, quantitative yield, contaminated with salts) as a pale yellow sticky solid. MS (m/z): 207.1 (M+H)+−.

Workup

  1. concentrationconcentrated
  2. additiondiluted with a small amount of water
  3. filtrationfiltered
  4. extractionextracted twice with dichloromethane
  5. concentrationThe aqueous phase was concentrated
  6. customthe residue was triturated in methanol (with traces of acetone)
  7. filtrationAfter filtration
  8. concentrationthe mother liquid was concentrated
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-e6ec1f11e7994cf6913ababd86f2c85f
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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