Water → 4-Fluorobenzenesulfonic acid

HRID 1823789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1823789
FC(F)(F)C(O)=O.C(OC(N(CC1C=CC(OC)=C(Cl)C=1)C1NC2C=C([O:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])C=CC=2N=1)=O)(C)(C)C.C(=O)(O)[O-].[Na+].O>ClCCl>[F:35][C:32]1[CH:31]=[CH:30][C:29]([S:26]([OH:28])(=[O:25])=[O:27])=[CH:34][CH:33]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 865960824-fluoro-benzenesulfonic acid 2-[tert-butoxycarbonyl-(3-chloro-4-methoxy-benzyl)-amino]-3H-benzoimidazol-5-yl ester

Produkt 1

HCID 468864-Fluorobenzenesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (1 ml) was added to a solution of 4-fluoro-benzenesulfonic acid 2-[tert-butoxycarbonyl-(3-chloro-4-methoxy-benzyl)-amino]-3H-benzoimidazol-5-yl ester (67 mg) in dichloromethane (4 ml). After cooling, the mixture was neutralised by addition of saturated sodium bicarbonate solution. Water (10 ml) was added and the solution extracted three times with dichloromethane (10 ml). The combined extracts were dried over magnesium sulfate and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1, v/v) to give 4-fluoro-benzenesulfonic acid 2-(3-(chloro-4-methoxy-benzylamino)-3H-benzoimidazol-5-yl ester (53 mg) as an off-white solid. Mass spectrum: 462 [M+H]+; retention time=7.69 minutes.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe solution extracted three times with dichloromethane (10 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customevaporated
  5. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1

Quellen und Nachweise

ORD-Eintrag
ord-f9f2180826a24c2ab08eb57de4a8983f
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041668B2

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