Trifluoroacetic acid → [4-ethyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid

HRID 1502152Notes

Reaction equation

HRID 1502152 reaction equation
C([O:5][C:6](=[O:21])[CH2:7][C:8]1[CH:9]=[N:10][C:11]([N:16]2[CH:20]=[N:19][N:18]=[N:17]2)=[CH:12][C:13]=1[CH2:14][CH3:15])(C)(C)C.C1(SC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:14]([C:13]1[CH:12]=[C:11]([N:16]2[CH:20]=[N:19][N:18]=[N:17]2)[N:10]=[CH:9][C:8]=1[CH2:7][C:6]([OH:21])=[O:5])[CH3:15]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 125491612tert-butyl [4-ethyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate

Product 1

HCID 89619191[4-ethyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[4-ethyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate (165 mg, 0.570 mmol) in DCM containing thioanisole (0.405 ml, 3.42 mmol) was added TFA (0.879 ml, 11.41 mmol) at 0° C. The mixture was stirred at RT overnight, concentrated. The residue was triturated with ether:hexane (1:1) to give [4-ethyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid: LC-MS: [(M+1]+=234.17.

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with ether:hexane (1:1)

Sources & evidence

ORD record
ord-f75e81ce4c6e4cb792db4c1f9d24b391
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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