Lithium hydroxide, monohydrate → HCID 51042704, compound

HRID 1875723Notes

Reaction equation

HRID 1875723 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[C:17]([C:18]3[N:22]([CH2:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:21]4[CH:30]=[C:31]([F:35])[C:32]([F:34])=[CH:33][C:20]=4[N:19]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:6][CH:5]=1.O.[OH-].[Li+]>O1CCCC1.O>[CH:24]1([CH2:23][N:22]2[C:21]3[CH:30]=[C:31]([F:35])[C:32]([F:34])=[CH:33][C:20]=3[N:19]=[C:18]2[C:17]2[C:12]([O:11][CH2:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:36])=[O:2])=[CH:5][CH:6]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67049941HCID 67049941, compound

Product 1

HCID 51042704HCID 51042704, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-[3-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-yloxymethyl]-benzoic acid methyl ester (84 mg, 0.17 mmol) in tetrahydrofuran (20 ml) and water (10 ml) was treated with an aqueous solution of lithium hydroxide monohydrate (36 mg, 0.86 mmol) and stirred at 25° C. for 2 h. The solvent removed in vacuo, the resulting crude material diluted with water (5 ml) and acidified with 2M aqueous hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by column chromatography over silica gel (50% ethyl acetate/n-hexane) to afford the final compound as an off-white powder (26%). MS (Turbo Spray): m/z=478.4 (M+H).

Workup

  1. customThe solvent removed in vacuo
  2. additionthe resulting crude material diluted with water (5 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography over silica gel (50% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-5d5b8ed24b0b414b950b03d646cc6780
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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