Hydrochloric Acid → HCID 86671822, Verbindung

HRID 2408927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2408927
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH:17][O:18][CH3:19].Cl.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13](=[O:15])[N:17]([O:18][CH3:19])[CH3:16])[CH2:10][CH2:11][CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 1512646Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 86671822HCID 86671822, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid (3 g, 13.94 mmol) in dry DMF (50 mL) was added N,O-dimethylhydroxylamine×HCl (1.36 g, 13.94 mmol) and DIEA (9.21 mL, 55.75 mmol). The reaction flask was cooled to 0° C. and after 10 minutes HATU (5.30 g, 13.94 mmol) was added to the solution (which turned yellow on addition). After 2 hrs the DMF was removed by rotary evaporation at reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed twice with 10% citric acid (aq) and saturated NaHCO3(aq) solution. The organic phase was dried with Na2SO4, filtered and evaporated on silica. The product was purified by flash chromatography (heptane: ethyl acetate (1:1) to give the product as a colourless oil that slowly crystallizes (3.13 g) in 87% yield.

Aufarbeitung

  1. additionwas added to the solution (which turned yellow on addition)
  2. customAfter 2 hrs the DMF was removed by rotary evaporation at reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed twice with 10% citric acid (aq) and saturated NaHCO3(aq) solution
  5. dry with materialThe organic phase was dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated on silica
  8. customThe product was purified by flash chromatography (heptane: ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3525fe8c1c11478d9666bd8e3724b0f0
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815809B2

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