Lithium hydroxide, monohydrate → 3-{[Ethyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoic Acid

HRID 349092

Reaction equation

HRID 349092 reaction equation
[CH2:1]([N:3]([CH2:21][CH2:22][CH3:23])[C:4]([C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]2[O:17][CH:18]=[CH:19][N:20]=2)[CH:15]=1)[C:9]([O:11]C)=[O:10])=[O:5])[CH3:2].O.[OH-].[Li+]>O1CCCC1.CO.O.C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:21][CH2:22][CH3:23])[C:4]([C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]2[O:17][CH:18]=[CH:19][N:20]=2)[CH:15]=1)[C:9]([OH:11])=[O:10])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21086182Methyl 3-{[ethyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate

Product 1

HCID 210858313-{[Ethyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoic Acid

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To methyl 3-{[ethyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate (375 mg, 1.2 mmol) in tetrahydrofuran/methanol/water (1:1:1, 9 mL) is added lithium hydroxide monohydrate (100 mg, 2.4 mmol), and the reaction is stirred at room temperature 16 h. The solution is diluted in chloroform and washed with water and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 301.1 [M−H]−.

Workup

  1. washwashed with water and saturated sodium chloride
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-960260c216e140af8939643ca3840351
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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