Lithium Hydroxide → HCID 66654834, compound

HRID 517743Notes

Reaction equation

HRID 517743 reaction equation
[OH-].[Li+].C([O:6][CH2:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[N:11]=[N:10][N:9]=1)(=O)C>C(O)C.O>[F:22][C:19]([F:20])([F:21])[C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:8]([CH2:7][OH:6])=[N:9][N:10]=[N:11]2)=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86691882HCID 86691882, compound2×

Product 1

HCID 66654834HCID 66654834, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (0.30 g, 12.5 mmol) was added at 0° C. to a solution of {1-[5-(trifluoromethyl)-2-pyridinyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 57, 1.80 g, 6.27 mmol) in a mixture of ethanol and water (2:1). The reaction mixture was stirred for 3 hr at room temperature. The ethanol was removed under reduced pressure. The residue was diluted with DCM and washed with ice-water, saturated NaHCO3 solution and brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. This was purified by column chromatography (60-120 mesh silica gel), eluting with 30% ethyl acetate/pet ether, to give the title compound (0.90 g).

Workup

  1. customThe ethanol was removed under reduced pressure
  2. additionThe residue was diluted with DCM
  3. washwashed with ice-water, saturated NaHCO3 solution and brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customThis was purified by column chromatography (60-120 mesh silica gel)
  8. washeluting with 30% ethyl acetate/pet ether

Sources & evidence

ORD record
ord-e3d7747d689547c2843d7f3ff76d1ee1
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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