Lithium hydroxide, monohydrate → 5-([Butyl(methyl)amino]methyl)thiophene-2-carboxylic acid

HRID 14109Notes

Reaction equation

HRID 14109 reaction equation
[CH2:1]([N:5]([CH2:7][C:8]1[S:12][C:11]([C:13]([O:15]C)=[O:14])=[CH:10][CH:9]=1)[CH3:6])[CH2:2][CH2:3][CH3:4].O.[OH-].[Li+]>O1CCOCC1.CO.O>[CH2:1]([N:5]([CH2:7][C:8]1[S:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=1)[CH3:6])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21086213Methyl 5-{[butyl(methyl)amino]methyl}thiophene-2-carboxylate

Product 1

HCID 210859605-([Butyl(methyl)amino]methyl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22592949Dioxane methanol waterSolvent

Procedure

To a solution of methyl 5-{[butyl(methyl)amino]methyl}thiophene-2-carboxylate (280 mg, 1.16 mmol) in 2:1:1 dioxane/methanol/water (8.0 mL) is added lithium hydroxide monohydrate (146 mg, 3.38 mmol) and the reaction mixture stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure and the solid residue partitioned between ethyl acetate and water The aqueous phase is acidified to pH 1 with 1 N hydrochloric acid and extracted several times with 3:1 chloroform/2-propanol. The combined organic phase is washed with water, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the title compound in pure form. 1H NMR (300 MHz, CD3OD) δ 7.75 (d, J=4 Hz, 1H), 7.41 (d, J=4 Hz, 1H), 4.63 (s, 2H), 3.20-3.14 (m, 2H), 2.85 (s, 3H), 1.82-1.72 (m, 2H), 1.42 (tq, J 8, 7 Hz, 2H), 0.99 (t, J=7 Hz, 3H).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe solid residue partitioned between ethyl acetate and water The aqueous phase
  3. extractionextracted several times with 3:1 chloroform/2-propanol
  4. washThe combined organic phase is washed with water, and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20865a8c4a14413789b892645753aa5d
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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