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Trifluoromethanesulfonic acid → XB 513

HRID 1034168
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1034168
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[CH2:24][CH2:23]2)[C:9]([N+:36]([O-:38])=[O:37])=[C:8]([CH3:39])[NH:7][C:6]=1[NH2:40])=[O:4].FC(F)(F)S(O)(=O)=[O:44].ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[CH2:24][CH2:23]2)=[O:44])[C:9]([N+:36]([O-:38])=[O:37])=[C:8]([CH3:39])[NH:7][C:6]=1[NH2:40])=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 62406Trifluoromethanesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 44210117HCID 44210117, Verbindung

Produkt 1

HCID 183813XB 513

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a 4-neck 500 ml round-bottom flask fitted with an addition funnel, thermometer and mechanical stirrer under a nitrogen atmosphere, was added 5.00 g of 2-amino-1,4-dihydro-4-(2-{4-[4-(2-methoxyphenyl)-1-piperazinyl]-butylthio}phenyl)-6-methyl-5-nitro-3-pyridinecarboxylic acid methyl ester and 120 ml of dichloromethane, followed by 1.73 ml of trifluoromethanesulfonic acid. The reaction mixture was cooled to -10° C. with an ice/acetone bath, and 1.88 g of 80% m-chloroperbenzoic acid in 120 ml of dichloromethane was added dropwise, maintaining -5° to -10° C. The reaction was stirred for an additional 2 hr. at -10° C. after the addition was complete. The reaction mixture was poured into conc. sodium bicarbonate, and the reaction flask was rinsed with acetone. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to an orange oil. The product (Ex. No. 2, Table 1) was isolated after column chromatography on silica gel, eluting with 20% methanol in ethyl acetate as an orange foam, 2.8 g. 1H-NMR (CDCl3) δ 1.84-2.05(m,2H); 2.03-2.05(m,2H); 2.36(s,3H); 2.55(t,2H,J=7 Hz); 2.71(br s,4H); 3.00-3.18(br s,6H); 3.61(s,3H); 3.85(s,3H); 5.76(s,1H); 6.70(br s,2H); 6.83-7.03(m,4H); 7.28-7.41(m,4H); 7.82-7.86(m,1H). Mass spectrum: 584 (M+1).

Aufarbeitung

  1. customTo a 4-neck 500 ml round-bottom flask fitted with an addition funnel
  2. temperaturemaintaining -5° to -10° C
  3. additionat -10° C. after the addition
  4. washthe reaction flask was rinsed with acetone
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an orange oil
  9. custom2, Table 1) was isolated after column chromatography on silica gel
  10. washeluting with 20% methanol in ethyl acetate as an orange foam, 2.8 g

Quellen und Nachweise

ORD-Eintrag
ord-26051bea1c7747d69f5bc04ed1957a1c
Quelldatensatz
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05314887

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