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Heptane → ethanesulfonic acid (3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]pyridin-4-yl)methylamide

HRID 634616
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 634616
[CH3:1][NH:2][S:3]([CH2:6][CH3:7])(=[O:5])=[O:4].[H-].[Na+].[CH3:10][C:11]1([CH3:22])[O:20][C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[CH:13]2[O:21][CH:12]12.CCCCCCC>CS(C)=O.C(OCC)(=O)C>[OH:21][CH:12]1[C:11]([CH3:22])([CH3:10])[O:20][C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[CH:13]1[CH2:1][NH:2][S:3]([CH2:6][CH3:7])(=[O:5])=[O:4]
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Komponenten

7

Edukt 4

HCID 8900HeptaneHCID 24758Sodium hydrideHCID 108560303,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-pyrano[3,2-c]pyridineHCID 11105495N-methylethane-1-sulfonamide

Produkt 1

HCID 86756350ethanesulfonic acid (3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]pyridin-4-yl)methylamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 480 mg (3.5 mmol) of N-methylethylsulfonamide in 0.75 ml DMSO (dimethylsulfoxide) is added to a suspension of 27 mg (0.7 mmol) of NaH (60% strength) in 1.5 ml of DMSO. After stirring at room temperature for 2 h, a solution of 0.48 g (2.7 mmol) of 2,2-dimethyl-1a,7b-dihydro-2H-1,3-dioxa-6-aza-cyclo-propa[a]naphthalene (prepared analogously to G. Burell et al. J. Med. Chem. 33 (1990) 3023-3027) in 6 ml of DMSO is added dropwise. The mixture is heated at 60° C. for 4 h and then stirred overnight at room temperature. The reaction mixture is added to ice water and extracted with ethyl acetate. After removing the solvent in vacuo, the solid obtained is stirred with a mixture of heptane and ethyl acetate and filtered off with suction. 400 mg (67%) of ethanesulfonic acid (3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]pyridin-4-yl)methylamide are obtained as a solid (m.p. 163° C.).

Aufarbeitung

  1. temperatureThe mixture is heated at 60° C. for 4 h
  2. stirringstirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. customAfter removing the solvent in vacuo
  5. customthe solid obtained
  6. filtrationfiltered off with suction

Quellen und Nachweise

ORD-Eintrag
ord-da3477a59af8404382f80ebffa92d067
Quelldatensatz
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06184221B2

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