Ethyl orthoformate → HCID 67517372, compound

HRID 2173404Notes

Reaction equation

HRID 2173404 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:12][CH3:13].[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(O)=O>[CH3:13][O:12][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:7][C:2]=1[N:1]1[CH:14]=[N:26][N:25]=[N:24]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 18959618HCID 18959618, compound

Product 1

HCID 67517372HCID 67517372, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution (4-amino-3-methoxyphenyl)acetic acid (1.63 g, 9.006 mmol) and triethyl orthoformate (4.0 g, 27.018 mmol) in 100 mL of HOAc was added sodium azide (644 mg, 9.907 mmol) and heated to 100° C. overnight. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated to give [3-methoxy-4-(1H-tetrazol-1-yl)phenyl]acetic acid, which was used for next step without purification.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7bd007f23aed403db7ba206d6646b94f
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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