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

HRID 14109

반응식

HRID 14109 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 22592949Dioxane methanol water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-20865a8c4a14413789b892645753aa5d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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