Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate → 3-[(Dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoic Acid

HRID 14305

Reaction equation

HRID 14305 reaction equation
[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:6])[CH2:2][CH3:3]>O1CCCC1.CO.O.O.[OH-].[Li+]>[CH2:22]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:6])[CH2:23][CH3:24]

Participants

4

Reactant 1

HCID 21086169Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate

Product 1

HCID 210857833-[(Dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoic Acid

Reagents, catalysts & solvents 2

HCID 168937Lithium hydroxide, monohydrateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate (4.4 g, 12.8 mmol) is dissolved in 1:1:1 tetrahydrofuran/methanol/water (60 mL), and lithium hydroxide monohydrate is added (1.1 g, 25.6 mmol), and the reaction stirred 15 min. The solution is concentrated under reduced pressure and diluted in chloroform. The solution is washed with water and saturated sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 333.1 [M+H]+.

Workup

  1. additionis added (1.1 g, 25.6 mmol)
  2. concentrationThe solution is concentrated under reduced pressure
  3. additiondiluted in chloroform
  4. washThe solution is washed with water and saturated sodium bicarbonate
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4fb70e28143a441893afb610343e3a5c
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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