Lithium hydroxide, monohydrate → HCID 10388029, compound

HRID 1432433Notes

Reaction equation

HRID 1432433 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]12[CH2:15][CH2:14][C:11]([C:16]3[NH:17][C:18]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=4)=[C:19]([C:21]4[CH:29]=[CH:28][C:24]5[O:25][CH2:26][O:27][C:23]=5[CH:22]=4)[N:20]=3)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)=[O:7]>C1COCC1.CO.O>[O:25]1[C:24]2[CH:28]=[CH:29][C:21]([C:19]3[N:20]=[C:16]([C:11]45[CH2:14][CH2:15][C:8]([C:6]([OH:7])=[O:5])([CH2:9][CH2:10]4)[CH2:13][CH2:12]5)[NH:17][C:18]=3[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=3)=[CH:22][C:23]=2[O:27][CH2:26]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11539569HCID 11539569, compound

Product 1

HCID 10388029HCID 10388029, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Lithium hydroxide monohydrate (0.020 g, 0.487 mmol) was added to a solution of 4-[4-benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl]-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (see Example 21; 0.150 g, 0.325 mmol) in a mixture of THF/MeOH/H2O (2/1/1, 4 mL). The mixture was stirred for 3 hours. Solvent was removed. Residue was diluted with water (30 mL). Citric acid was added to the solution to make the pH lower than 7. The aqueous solution was extracted with ethyl acetate. Ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered and concentrated to give 0.140 g (99%) of the title compound as a yellow solid. MS (ESP+) m/z 432.2 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.72 (m, 1H), 7.33 (d, 1H, J=7.7 Hz), 7.22 (d, 1H, J=7.7 Hz), 6.98 (m, 3H), 6.05 (s, 2H), 2.64 (s, 3H), 2.11 (m, 6H), 1.99 (m, 6H).

Workup

  1. customSolvent was removed
  2. additionResidue was diluted with water (30 mL)
  3. additionCitric acid was added to the solution
  4. extractionThe aqueous solution was extracted with ethyl acetate
  5. extractionEthyl acetate extract
  6. washwas washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ed4f9e7520044c8a99b1c014c1d5c3f0
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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