Lithium Hydroxide → 3-((dipropylamino)carbonyl]-5-[1-(ethoxymethyl)-1H-imidazol-2-yl]benzoic acid

HRID 14074Notes

Reaction equation

HRID 14074 reaction equation
[CH2:1]([N:4]([CH2:26][CH2:27][CH3:28])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[N:18]([CH2:22][O:23][CH2:24][CH3:25])[CH:19]=[CH:20][N:21]=2)[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:6])[CH2:2][CH3:3].[OH-].[Li+]>O1CCCC1.CO.O>[CH2:26]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[N:18]([CH2:22][O:23][CH2:24][CH3:25])[CH:19]=[CH:20][N:21]=2)[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:6])[CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21086170Methyl 3-[(dipropylamino)carbonyl)-5-[1-(ethoxymethyl)-1H-imidazol-2-yl]benzoate

Product 1

HCID 210857843-((dipropylamino)carbonyl]-5-[1-(ethoxymethyl)-1H-imidazol-2-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of the ester from step 1 (756 mg, 1.95 mmol) in 2:1:1 tetrahydrofuran/methanol/water (12 mL) is added lithium hydroxide (170 mg, 4 mmol). The reaction mixture is stirred at room temperature for 42 h, and concentrated under reduced pressure. The residue is partitioned between water (10 mL) and chloroform (10 mL). The aqueous layer is acidified to pH 4-5 with 1 N hydrochloric acid and extracted with 3:1 chloroform/2-propanol (3×30 mL). The combined organic layers are dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CD3OD) δ 8.51 (s, 1H), 8.06 (s, 1H), 8.00 (s, 1H), 7.49 (s, 1H), 7.17 (s, 1H), 5.39 (s, 2H), 3.62 (q, J=7 Hz, 2H), 3.51 (m, 2H), 3.27 (m, 2H), 1.72 (m, 2H), 1.59 (m, 2H), 1.21 (t, J=7 Hz, 3H), 1.00 (m, 3H), 0.75 (m, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is partitioned between water (10 mL) and chloroform (10 mL)
  3. extractionextracted with 3:1 chloroform/2-propanol (3×30 mL)
  4. dry with materialThe combined organic layers are dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6402a874e4384f5a8838dbe1c8fe1777
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

Loading…