1,1,3,3-Tetramethylguanidine → HCID 69512532, Verbindung

HRID 1247531

Reaktionsgleichung

Reaktionsgleichung von HRID 1247531
[CH3:1][O:2][C:3](=[O:19])[CH:4]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])P(OC)(OC)=O.CN(C)C(=N)N(C)C.[N+:28]([C:31]1[C:32]([CH:37]=O)=[N:33][CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29]>C1COCC1.O>[C:15]([O:14][C:12]([NH:11][C:4](=[CH:37][C:32]1[C:31]([N+:28]([O-:30])=[O:29])=[CH:36][CH:35]=[CH:34][N:33]=1)[C:3]([O:2][CH3:1])=[O:19])=[O:13])([CH3:16])([CH3:17])[CH3:18]

Komponenten

6

Edukt 3

HCID 664601,1,3,3-TetramethylguanidineHCID 3293613-NitropicolinaldehydeHCID 397380Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetate

Produkt 1

HCID 69512532HCID 69512532, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Methyl[(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate (1.33 g, 4.46 mmol) was dissolved in dry THF (20 mL) and cooled to −78° C. under nitrogen. Tetramethylguanidine (490 mg, 4.26 mmol) was added and the solution stirred at −78° C. for a further 10 mins. A solution of 3-nitropyridine-2-carbaldehyde (Tetrahedron vol 0.54 (1998) p 6311) (618 mg, 4.06 mmol) in dry THF (5 mL.) was added drop wise. After stirring the solution for 2 hours. at −78° C. (50 mL) it was diluted with water (150 mL) and extracted with ethyl acetate. The combined extracts were washed with water (2×20 mL) and brine (20 mL), dried (MgSO4) and evaporated under reduced pressure to give a yellow oil, which was purified by column chromatography (DCM) to give the title compound as a 4:1 mixture of Z/E isomers (1.1 g, 84%).

Aufarbeitung

  1. stirringAfter stirring the solution for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water (2×20 mL) and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give a yellow oil, which
  7. customwas purified by column chromatography (DCM)

Quellen und Nachweise

ORD-Eintrag
ord-decac563749744449299c313e0f43013
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129249B2

Verknüpfte Notizen

Wird geladen…