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

HRID 14299Notes

Reaction equation

HRID 14299 reaction equation
[CH2:1]([N:5]([CH3:23])[C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([C:18]2[O:19][CH:20]=[CH:21][N:22]=2)[CH:17]=1)[C:11]([O:13]C)=[O:12])=[O:7])[CH2:2][CH2:3][CH3:4].O.[OH-].[Li+]>O1CCCC1.CO.O.C(Cl)(Cl)Cl>[CH2:1]([N:5]([CH3:23])[C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([C:18]2[O:19][CH:20]=[CH:21][N:22]=2)[CH:17]=1)[C:11]([OH:13])=[O:12])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21086164Methyl 3-{[butyl(methyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate

Product 1

HCID 210857323-{[Butyl(methyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoic Acid

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To methyl 3-{[butyl(methyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate (660 mg, 2.1 mmol) in tetrahydrofuran/methanol/water (1:1:1, 9 mL) is added lithium hydroxide monohydrate (175 mg, 4.2 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-dc9230143563407a82a9b2ed3ae842f5
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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