Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)propionate → 3-(Tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

HRID 47214Notes

Reaction equation

HRID 47214 reaction equation
[NH2:1][C:2](=[N:11][O:12][C:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22])=O)[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]>C1(C)C=CC=CC=1>[C:7]([O:6][C:4]([CH2:3][C:2]1[N:1]=[C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:20]=2[C:21]([F:24])([F:23])[F:22])[O:12][N:11]=1)=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

3

Reactant 1

HCID 53931299Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)propionate

Product 1

HCID 227440793-(Tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazoleYield 54.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

28 g of tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate are dissolved in 380 ml of toluene and heated under reflux for 17 hours. Concentration and chromatographic purification of the residue over silica gel gives 14.4 g of the product as a pale brown oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 17 hours
  3. concentrationConcentration and chromatographic purification of the residue over silica gel

Sources & evidence

ORD record
ord-53b60f67e14a45308a321a903bf2cf53
Source dataset
uspto-grants-2004_03
Patent number
US06699853B2

Reaction notes

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