Hydrochloric Acid → HCID 57467323, Verbindung

HRID 1044521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044521
FC1C=C(C=CC=1)CC1C2C(=CC=C(CCCNS(CCC)(=O)=O)C=2)CCC1NC(=O)[O-].CI.C(=O)([O-])[O-].[Cs+].[Cs+].[F:41][C:42]1[CH:43]=[C:44]([CH:75]=[CH:76][CH:77]=1)[CH2:45][CH:46]1[C:55]2[C:50](=[CH:51][CH:52]=[C:53]([CH2:56][CH2:57][CH2:58][N:59]([CH3:66])[S:60]([CH2:63][CH2:64][CH3:65])(=[O:62])=[O:61])[CH:54]=2)[CH2:49][CH2:48][CH:47]1[NH:67]C(=O)OC(C)(C)C.[ClH:78]>C(#N)C.C(OCC)(=O)C.C(O)(C)C>[ClH:78].[NH2:67][CH:47]1[CH:46]([CH2:45][C:44]2[CH:75]=[CH:76][CH:77]=[C:42]([F:41])[CH:43]=2)[C:55]2[CH:54]=[C:53]([CH2:56][CH2:57][CH2:58][N:59]([CH3:66])[S:60]([CH2:63][CH2:64][CH3:65])(=[O:62])=[O:61])[CH:52]=[CH:51][C:50]=2[CH2:49][CH2:48]1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 57467325HCID 57467325, VerbindungHCID 68513853tert-butyl 1-(3-fluorobenzyl)-7-(3-(N-methylpropylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

Produkt 1

HCID 57467323HCID 57467323, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3776IsopropanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

tert-Butyl (1-(3-fluorobenzyl)-7-(3-(propylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (cf. 209 and 201a, 65 mg, 0.125 mmol) was dissolved in acetonitrile (800 μL) and methyl iodide (24 μL, 0.376 mmol) and cesium carbonate (0.102 g, 0.313 mmol) was added. The reaction mixture was heated for 24 hours in a sealed vessel to 80° C. The reaction mixture was diluted with ethyl acetate. The ethyl acetate solution was successively washed with water and saturated sodium chloride solution. The organic phase was dried (MgSO4) and concentrated in vacuo. The crude product was purified by preparative thin-layer chromatography (silica gel, dichloromethane, methanol). The obtained tert-butyl 1-(3-fluorobenzyl)-7-(3-(N-methylpropylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (65 mg, 0.122 mmol) was dissolved in 4 M hydrochloric acid in isopropanol and stirred at room temperature for 4 hours. The solvent was removed in vacuo. Diethyl ether was added and the precipitate removed by filtration and dried. Yield: 22 mg (0.047 mmol, 38%).

Aufarbeitung

  1. washThe ethyl acetate solution was successively washed with water and saturated sodium chloride solution
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by preparative thin-layer chromatography (silica gel, dichloromethane, methanol)
  5. customThe solvent was removed in vacuo
  6. additionDiethyl ether was added
  7. customthe precipitate removed by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c3b163f1de1147d59b3bcec55b29922b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563617B2

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