4-Hydroxybenzoic Acid → HCID 86638568, Verbindung

HRID 1807776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807776
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[F:11][C:12]([F:33])([F:32])[C:13]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1)([OH:18])[C:14]([F:17])([F:16])[F:15].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[F:33][C:12]([F:11])([F:32])[C:13]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=3)=[O:8])[CH2:28][CH2:27]2)=[CH:23][CH:24]=1)([OH:18])[C:14]([F:17])([F:16])[F:15]

Komponenten

6

Edukt 4

HCID 1354-Hydroxybenzoic AcidHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 866385661,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol

Produkt 1

HCID 86638568HCID 86638568, VerbindungAusbeute 9,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Hydroxybenzoic acid (2.045 mmol, 0.282 g), 1,1,1,3,3,3-hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol (2.045 mmol, 0.7 g) and triethylamine (6.14 mmol, 0.853 mL, 0.621 g) were combined and stirred at room temperature in dichloromethane (5 mL). 1-Propanephosphonic acid cyclic anhydride (3.07 mmol, 1.826 mL, 1.952 g; 50% solution in ethyl acetate) was added and the reaction stirred for 2 hours. The reaction mixture was washed with saturated sodium bicarbonate solution and the organic layer dried over magnesium sulphate and concentrated under vacuum. The residue was dissolved in dichloromethane with a few drops of methanol and purified by column chromatography (dichloromethane—6% methanol in dichloromethane) to afford the title compound (90 mg). MS (ESI) m/z 463.0 [M+H]+

Aufarbeitung

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  2. dry with materialthe organic layer dried over magnesium sulphate
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane with a few drops of methanol
  5. custompurified by column chromatography (dichloromethane—6% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-1e37f71bf7a14fbe9d4f72e059cd3e30
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357679B2

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