Ethyl orthoformate → [2,5-difluoro-4-(1H-tetrazol-1-yl)phenyl]acetic acid

HRID 2173390Notes

Reaction equation

HRID 2173390 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][C:10]([OH:12])=[O:11])=[C:4]([F:13])[CH:3]=1.[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(O)=O>[F:13][C:4]1[CH:3]=[C:2]([N:1]2[CH:14]=[N:26][N:25]=[N:24]2)[C:7]([F:8])=[CH:6][C:5]=1[CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 675159132-(4-Amino-2,5-difluorophenyl)acetic acid

Product 1

HCID 89754696[2,5-difluoro-4-(1H-tetrazol-1-yl)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (4-amino-2,5-difluorophenyl)acetic acid (380 mg, 2.0 mmol) and triethyl orthoformate (902 mg, 6.1 mmol) in HOAc (10 mL) was added sodium azide (158 mg, 2.44 mmol) and the mixture was heated to 100° C. for 3 hours. After the reaction was completed, the reaction mixture was cooled to ambient temperature. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The [2,5-difluoro-4-(1H-tetrazol-1-yl)phenyl]acetic acid was directly used in next step.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-349b90cec86f4907b0e538fe9ef705ea
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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