HCID 22417270, compound → HCID 22417281, compound

HRID 1647072Notes

Reaction equation

HRID 1647072 reaction equation
[CH3:1][C:2]([N:5]1[N:9]=[N:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[CH:13][CH:12]=2)=[N:6]1)([CH3:4])[CH3:3]>FC(F)(F)C(O)=O>[CH3:4][C:2]([N:5]1[N:9]=[N:8][C:7]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:16]=2)=[N:6]1)([CH3:1])[CH3:3]

Participants

3

Reactant 1

HCID 22417270HCID 22417270, compound

Product 1

HCID 22417281HCID 22417281, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-dimethylethyl 4-[[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]methyl]benzenepropanoate (3.0 g, 8.7 mmol) was dissolved in trifluoroacetic acid (33 mL) and stirred at room temperature under argon for 12 hours. The mixture was concentrated and then dissolved in water (50 ml). After adding enough sat. NaHCO3 to raise the pH to 8, the solution was washed with diethyl ether (2×25 mL). The aqueous layer was acidified to pH 3 with 1N HCl and the product collected by suction filtration. Recrystallization from hexanes gave 4-[[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]methyl]benzene-propanoic acid (1.5 g, 5.7 mmol) in 66% yield, mp. 139°-141° C.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in water (50 ml)
  3. additionAfter adding enough sat. NaHCO3
  4. temperatureto raise the pH to 8
  5. washthe solution was washed with diethyl ether (2×25 mL)
  6. filtrationthe product collected by suction filtration
  7. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-56659bb6216e4b02a810e034fa658349
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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