Lithium hydroxide, monohydrate → 4-(3-Naphthalen-1-ylmethyl-2,3-dihydro-imidazo[1,2-a]pyridin-2-ylsulfanyl)-butyric acid

HRID 215970Notes

Reaction equation

HRID 215970 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][S:7][CH:8]1[CH:16]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[N:9]1.O.[OH-].[Li+]>C1COCC1.O>[C:18]1([CH2:17][CH:16]2[N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]3=[N:9][CH:8]2[S:7][CH2:6][CH2:5][CH2:4][C:3]([OH:28])=[O:2])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 687023894-(3-Naphthalen-1-ylmethyl-2,3-dihydro-imidazo[1,2-a]pyridin-2-ylsulfanyl)-butyric acid methyl ester

Product 1

HCID 687026464-(3-Naphthalen-1-ylmethyl-2,3-dihydro-imidazo[1,2-a]pyridin-2-ylsulfanyl)-butyric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 50 mg (0.13 mmol) of 4-(3-naphthalen-1-ylmethyl-2,3-dihydro-imidazo[1,2-a]pyridin-2-ylsulfanyl)-butyric acid methyl ester in 2 mL of THF is treated with a solution of 11 mg (0.26 mmol) of lithium hydroxide monohydrate in 1 mL of water at room temperature. The resulting mixture is heated to 40° C., and stirred at this temperature for 3 h. Then the reaction mixture is cooled to room temperature and concentrated in vacuo. The residue is diluted with water and neutralized with 1N HCl solution. The product is extracted with ethyl acetate, and the organic layer is separated. The organic layer is washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography eluting with 3˜10% methanol in dichloromethane solution to give the title compound. LCMS (ESMS): m/z 377 (M+H+)

Workup

  1. temperatureThen the reaction mixture is cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue is diluted with water and neutralized with 1N HCl solution
  4. extractionThe product is extracted with ethyl acetate
  5. customthe organic layer is separated
  6. washThe organic layer is washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by flash chromatography
  11. washeluting with 3˜10% methanol in dichloromethane solution

Sources & evidence

ORD record
ord-945bd1b28a924d4c9cbf6dea5443c5b6
Source dataset
uspto-grants-2012_06
Patent number
US08193214B2

Reaction notes

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