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

HRID 14303

Reaction equation

HRID 14303 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-12ecfca733f9427082c89b0123cdd622
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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