Lithium hydroxide, monohydrate → 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoic acid

HRID 1175985Notes

Reaction equation

HRID 1175985 reaction equation
O.[OH-].[Li+].[N:4]1([C:8]([C:10]2[CH:11]=[C:12]([Cl:32])[C:13]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:31])[CH2:29][OH:30])[CH:26]=3)[C:20]([O:22]C)=[O:21])=[N:14][CH:15]=2)=[O:9])[CH2:7][CH2:6][CH2:5]1>O.C1COCC1>[N:4]1([C:8]([C:10]2[CH:11]=[C:12]([Cl:32])[C:13]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:31])[CH2:29][OH:30])[CH:26]=3)[C:20]([OH:22])=[O:21])=[N:14][CH:15]=2)=[O:9])[CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53629688methyl 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoate

Product 1

HCID 591271743-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (529 mg, 12.59 mmol) in water (25 mL) was added to a solution of methyl 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoate (5.3 g, 12.6 mmol) in THF (50 mL) and stirred at RT for 3 hours. The THF was removed in vacuo and the aqueous layer was washed with ethyl acetate (50 mL) to remove any impurities. The aqueous layer was acidified and extracted into ethyl acetate (2×50 mL), and the organics washed with brine, dried (MgSO4), and concentrated in vacuo to give the desired compound as a white foam (3.74 g).

Workup

  1. customThe THF was removed in vacuo
  2. washthe aqueous layer was washed with ethyl acetate (50 mL)
  3. customto remove any impurities
  4. extractionextracted into ethyl acetate (2×50 mL)
  5. washthe organics washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0dc6221eebe1458f8d088201638d72b7
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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