Lithium Hydroxide → HCID 89619108, compound

HRID 1502158Notes

Reaction equation

HRID 1502158 reaction equation
[OH-].[Li+].[CH3:3][C:4]1[N:8]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][C:16]([O:18]CC)=[O:17])=[N:13][CH:14]=2)[N:7]=[N:6][N:5]=1>O.C1COCC1>[CH3:3][C:4]1[N:8]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[N:13][CH:14]=2)[N:7]=[N:6][N:5]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89619119HCID 89619119, compound

Product 1

HCID 89619108HCID 89619108, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (161 mg, 3.84 mmol) dissolved in water (3 mL) was added to ethyl 2-(5-(5-methyl-1H-tetrazol-1-yl)pyridin-2-yl)acetate (776 mg, 3.14 mmol) in THF (10 ml) and stirred at room temperature. The reaction was followed by TLC. Evaporated off the organics without heating and cooled in ice bath then acidified with 1N HCL (3.84 ml, pH ˜3). Extracted with EtOAc/THF (2×), washed with brine (1×), dried over Na2SO4, filtered and concentrated to yield 2-(5-(5-methyl-1H-tetrazol-1-yl)pyridin-2-yl)acetic acid: 1H-NMR (500 MHz, CD3OD) δ ppm 8.79 (d, J=2.4 Hz, 1H), 8.098 (dd, J=8.0, 2.5 Hz, 1H), 7.710 (d, J=8.3 Hz, 1H), 3.978 (s, 2H), 2.649 (s, 3H)

Workup

  1. customEvaporated off the organics
  2. temperaturewithout heating
  3. temperaturecooled in ice bath
  4. extractionExtracted with EtOAc/THF (2×)
  5. washwashed with brine (1×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-97eade5caf7941e585d6b20d6388506b
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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