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

HRID 2173332Notes

Reaction equation

HRID 2173332 reaction equation
[N:1]1([C:6]2[N:7]=[CH:8][C:9]([CH2:12][C:13]([O:15]CC)=[O:14])=[N:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1.O[Li].O>C1COCC1.CO.O.O>[N:1]1([C:6]2[N:7]=[CH:8][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[N:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]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 diluted with 200 mL of water and washed with ether (30 mL*3). The water layer was acidified to pH=4 with diluted hydrochloric acid and extracted with EtOAc (50 mL*5). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to afford [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetic acid. 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. washwashed 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-e1f8d7db14a44ffa86913faa22a37d22
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…