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

HRID 14086Notes

Reaction equation

HRID 14086 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). The reaction is stirred 15 min and is concentrated under reduced pressure. The residue is diluted in chloroform and washed with water, brine, 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. concentrationis concentrated under reduced pressure
  3. additionThe residue is diluted in chloroform
  4. washwashed with water, brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-194750c907444fb2bcfefa079939d83d
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

Loading…