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3-Pyridinecarboxylic acid, 4-(trifluoromethyl)- → Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)propionate

HRID 1978981
Notes
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Reaction equation

HRID 1978981 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]([OH:11])=[O:10].C(C1NC=CN=1)(C1NC=CN=1)=O.[C:26]([O:30][C:31]([CH2:33][C:34](=[N:36]O)[NH2:35])=[O:32])([CH3:29])([CH3:28])[CH3:27]>C1COCC1>[NH2:36][C:34](=[N:35][O:10][C:9]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[C:2]([F:1])([F:12])[F:13])=[O:11])[CH2:33][C:31]([O:30][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 76589802tert-butyl 2-(N'-hydroxycarbamimidoyl)acetate

Product 1

HCID 53931299Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)propionateYield 51.6%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

30 g of 4-trifluoromethyl-3-pyridinecarboxylic acid is initially charged in 150 ml of dry THF and, a little at a time, admixed with 25.3 g of carbonyl-diimidazole. The mixture is stirred at room temperature for 30 min. 27.2 g of tert-butoxycarbonylacetamide oxime dissolved in 150 ml of THF are then added dropwise. The mixture is stirred overnight, the solvent is evaporated and the residue is taken up in ethyl acetate, washed three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. Concentration of the ethyl acetate phase gives 28 g of the product as a pale yellow solid.

Workup

  1. additionare then added dropwise
  2. stirringThe mixture is stirred overnight
  3. customthe solvent is evaporated
  4. washwashed three times with 1 M sulfuric acid

Sources & evidence

ORD record
ord-fdaa577ba9fd42aa8988ed42e6d7917c
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06239160B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes