Lithium hydroxide, monohydrate → [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetic acid

HRID 1502119Notes

Reaction equation

HRID 1502119 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[CH:11]=[N:10][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:8][N:7]=1)C.O[Li].O>C1COCC1.CO.O.O>[N:12]1([C:9]2[N:10]=[CH:11][C:6]([CH2:5][C:4]([OH:17])=[O:3])=[N:7][CH:8]=2)[CH:16]=[N:15][N:14]=[N:13]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 77230648ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate

Product 1

HCID 67517359[5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of ethyl[5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate (2.0 g, 8.5 mmol) in 60 mL of THF/MeOH/H2O (2:2:1) was added LiOH.H2O (540 mg, 12.8 mmol) portionwise and stirred for 30 minutes before diluting with 200 mL of water and washing with ether (30 mL×3). The water layer was acidified to pH=4 with diluted HCl and extracted with EtOAc (50 mL×5). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to afford title compound: 1H-NMR (400 MHz, d6-DMSO) δ ppm 12.93 (brs, 1H), 10.22 (s, 1H), 9.25 (d, J=1.2 Hz, 1H), 8.71 (d, J=1.2 Hz, 1H), 3.98 (s, 2H).

Workup

  1. washwashing with ether (30 mL×3)
  2. extractionextracted with EtOAc (50 mL×5)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a962cf963ec24a56b0875ad6e295c81b
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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