Citric Acid → HCID 67518044, compound

HRID 2173365Notes

Reaction equation

HRID 2173365 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([CH3:14])[C:9]([O:11]CC)=[O:10])=[CH:6][CH:5]=[C:4]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[N:3]=1.O[Li].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.C1COCC1.O>[CH3:1][C:2]1[C:7]([CH:8]([CH3:14])[C:9]([OH:11])=[O:10])=[CH:6][CH:5]=[C:4]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[N:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67517354HCID 67517354, compound

Product 1

HCID 67518044HCID 67518044, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of ethyl 2-[2-methyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]propanoate (300 mg, 1.1 mmol) in 8 mL of MeOH/THF/H2O (2:2:1) was added LiOH.H2O (75 mg, 1.8 mmol) and stirred for 30 min at room temperature. The reaction was acidified with citric acid until pH about 3˜4. Extracted with EtOAc, the combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give 2-[2-methyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]propanoic acid. 1H-NMR (400 MHz, CDCl3) δ ppm 9.51 (s, 1H), 7.86-7.91 (m, 2H), 4.00-4.05 (m, 1H), 2.64 (s, 3H), 1.57 (d, J=7.8 Hz, 3H).

Workup

  1. extractionExtracted with EtOAc
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0f960a1201d743fb99b5d0e5c3c3ea4b
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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