StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Oxalyl chloride → 2-(2-fluoro-4-methanesulfonyl-phenylsulfanyl)-N-[3-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-propionamide

HRID 1802430
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1802430
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:12][C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=O.C(Cl)(=O)C(Cl)=O.[CH3:25][O:26][CH2:27][C:28]([C:31]1[CH:35]=[C:34]([NH2:36])[O:33][N:32]=1)([CH3:30])[CH3:29].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(Cl)Cl.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[S:12][C:13]([CH3:18])([CH3:17])[C:14]([NH:36][C:34]1[O:33][N:32]=[C:31]([C:28]([CH3:30])([CH3:29])[CH2:27][O:26][CH3:25])[CH:35]=1)=[O:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 534418093-(1-Methoxy-2-methylpropan-2-YL)isoxazol-5-amineHCID 592679272-(2-Fluoro-4-methanesulfonyl-phenylsulfanyl)-2-methyl-propionic acid

Produkt 1

HCID 592678902-(2-fluoro-4-methanesulfonyl-phenylsulfanyl)-N-[3-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-propionamide
Ausbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Activation of 336 mg (1.15 mmol) of 2-(2-fluoro-4-methanesulfonyl-phenylsulfanyl)-2-methyl-propionic acid as its acid chloride is achieved by treatment with oxalyl chloride (0.3 mL, 3.45 mmol) and DMF (1 drop) in DCM (15 mL) at room temperature for 3 h. The solvent is removed under reduced pressure and the crude acid chloride is dissolved in toluene (5 mL) and added to a solution of 196 mg (1.15 mmol) of 3-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-5-ylamine and N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) in toluene. The reaction is heated to 50° C. for 18 h. After cooling to room temperature, the reaction mixture is diluted with ethyl acetate (20 mL) and washed with 1M aqueous HCl solution (2×10 mL), water (2×10 mL), saturated aqueous NaHCO3 solution (2×10 mL), brine (10 mL). The organic layer is dried (Na2SO4), filtered and the filtrate is concentrated under reduced pressure. The residue is purified twice by column chromatography (silica, eluent: heptanes, 20-50% ethyl acetate, followed by heptanes, 10% ethyl acetate) to afford 220 mg of 2-(2-fluoro-4-methanesulfonyl-phenylsulfanyl)-N-[3-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-propionamide. Yield: 43%, ES-MS: m/z 445 [M+H]

Aufarbeitung

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe crude acid chloride is dissolved in toluene (5 mL)
  3. temperatureAfter cooling to room temperature
  4. washwashed with 1M aqueous HCl solution (2×10 mL), water (2×10 mL), saturated aqueous NaHCO3 solution (2×10 mL), brine (10 mL)
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified twice by column chromatography (silica, eluent: heptanes, 20-50% ethyl acetate, followed by heptanes, 10% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-77fab2d387144e9eb2e748f881302845
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08349871B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion