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 487822Notes

Reaction equation

HRID 487822 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. NaHCO2 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 IN 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. NaHCO2
  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-4e05fe449ca5414297283564e7c8c004
Source dataset
uspto-grants-1994_03
Patent number
US05296608

Reaction notes

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