Trifluoroacetic acid → 3-(Hydroxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

HRID 47215Notes

Reaction equation

HRID 47215 reaction equation
C([O:5][C:6]([CH2:8][C:9]1[N:13]=[C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:19]=2[C:20]([F:23])([F:22])[F:21])[O:11][N:10]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:7][C:6]([CH2:8][C:9]1[N:13]=[C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:19]=2[C:20]([F:22])([F:23])[F:21])[O:11][N:10]=1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 227440793-(Tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

Product 1

HCID 227440893-(Hydroxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazoleYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.4 g of 3-(tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole are dissolved in 110 ml of dichloromethane and admixed with 57 ml of trifluoroacetic acid. The reaction mixture is stirred at room temperature for 1.5 hours and subsequently concentrated under reduced pressure. The residue is repeatedly taken up in dichloromethane and reconcentrated to remove any remaining trifluoroacetic acid. The mixture is finally triturated with diethyl ether, giving 8.1 g of the product as a white solid.

Workup

  1. concentrationsubsequently concentrated under reduced pressure
  2. customto remove any remaining trifluoroacetic acid
  3. customThe mixture is finally triturated with diethyl ether

Sources & evidence

ORD record
ord-ce1fa7c16f61454cb8b6378bc1b75663
Source dataset
uspto-grants-2004_03
Patent number
US06699853B2

Reaction notes

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