Trifluoroacetic acid → N-(3-(Aminomethyl)benzyl)-3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxybenzenesulfonamide

HRID 1889679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1889679
[Cl:1][C:2]1[C:3]([OH:43])=[C:4]([S:9]([N:12]([CH2:27][C:28]2[CH:29]=[C:30]([CH:40]=[CH:41][CH:42]=2)[CH2:31][NH:32]C(=O)OC(C)(C)C)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:32][CH2:31][C:30]1[CH:29]=[C:28]([CH:42]=[CH:41][CH:40]=1)[CH2:27][N:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[S:9]([C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[OH:43])(=[O:11])=[O:10]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 58531334tert-Butyl 3-((3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

Produkt 1

HCID 58531533N-(3-(Aminomethyl)benzyl)-3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxybenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

tert-Butyl 3-[(3,5-dichloro-N-((4′-fluorobiphenyl-4-yl)methyl]-2-hydroxyphenylsulfonamido) methyl)benzylcarbamate (1.0 g, 1.5 mmol, 1 eq) was dissolved in dry DCM, stirred for 10 minutes and cooled to 0° C. Trifluoroacetic acid (3.5 g, 309 mmol 20 eq) was added slowly at 0° C. The reaction mixture was stirred for 10 min and slowly brought to rt. After 4 h, the solvent was evaporated under reduced pressure, and ethyl acetate and 10% aq. NaHCO3 solution were added. The mixture was stirred for 10 minutes and the aqueous mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and evaporated under reduced pressure. The crude salt (0.7 g, 82%) was used immediately in the next step. 1H NMR (400 MHz, DMSO-d6) δ 3.52 (s, 2H), 4.44 (s, 2H), 4.46 (s, 2H), 6.9-6.99 (t, 2H), 7.08-7.10 (d, 2H), 7.17-7.20 (m, 4H), 7.22-7.27 (m, 2H), 7.44-7.46 (d, 2H), 7.6-7.65 (t, 2H). MS (ESI): 546.0 (M+H)+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 10 min
  2. customslowly brought to rt
  3. waitAfter 4 h
  4. customthe solvent was evaporated under reduced pressure, and ethyl acetate and 10% aq. NaHCO3 solution
  5. additionwere added
  6. stirringThe mixture was stirred for 10 minutes
  7. extractionthe aqueous mixture was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried with anhydrous Na2SO4
  9. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d1efcaa188e24c45bac9a2edd1e4b1d7
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501992B2

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