5-[4-(3-(1,1-dimethylethoxy)-3-oxopropyl)phenyl]-2-(1,1-dimethylethyl)-2H-tetrazole → 4-[2-(1,1-dimethylethyl)-2H-tetrazole-5-yl]benzenepropanoic acid

HRID 1647077Notes

Reaction equation

HRID 1647077 reaction equation
CC(C)([O:4][C:5](=[O:23])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[N:16][N:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[N:18]=2)=[CH:10][CH:9]=1)C>FC(F)(F)C(O)=O>[CH3:22][C:19]([N:17]1[N:16]=[N:15][C:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][C:5]([OH:23])=[O:4])=[CH:9][CH:10]=2)=[N:18]1)([CH3:20])[CH3:21]

Participants

3

Reactant 1

HCID 224172825-[4-(3-(1,1-dimethylethoxy)-3-oxopropyl)phenyl]-2-(1,1-dimethylethyl)-2H-tetrazole

Product 1

HCID 148887304-[2-(1,1-dimethylethyl)-2H-tetrazole-5-yl]benzenepropanoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-[4-(3-(1,1-dimethylethoxy)-3-oxopropyl)phenyl]-2-(1,1-dimethylethyl)-2H-tetrazole (1.0 g, 3.7 mmol) was dissolved in trifluoroacetic acid (14 mL) and stirred at room temperature under argon for 12 hours. The mixture was concentrated and then dissolved in water (35 ml). After adding enough sat. NaHCO3 to raise the pH to 8, the solution was washed with diethyl ether (2×10 mL). The aqueous layer was acidified to pH 3 with 1N HCl and the product was collected by suction filtration to give 4-[2-(1,1-dimethylethyl)-2H-tetrazole-5-yl]benzenepropanoic acid (0.7 g, 3.1 mmol) in 84% yield, mp. 88°-90° C.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in water (35 ml)
  3. additionAfter adding enough sat. NaHCO3
  4. temperatureto raise the pH to 8
  5. washthe solution was washed with diethyl ether (2×10 mL)
  6. filtrationthe product was collected by suction filtration

Sources & evidence

ORD record
ord-61aae5eafe444c1b89197ddfeba5b326
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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