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

HRID 1059495

Reaktionsgleichung

Reaktionsgleichung von HRID 1059495
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 53931299Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)propionateAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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 9 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ba86bc3513ab49a68d3c8d33a64876b1
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521610B2

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