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Hydrochloric Acid → Cyclopropanesulfonic acid 3-(2',4',5'-trifluoro-biphenyl-4-yloxymethyl)-benzoylamide

HRID 1665259
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1665259
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([OH:23])=O)=[CH:12][CH:11]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:39]1([S:42]([NH2:45])(=[O:44])=[O:43])[CH2:41][CH2:40]1.C1CCN2C(=NCCC2)CC1.Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([NH:45][S:42]([CH:39]2[CH2:41][CH2:40]2)(=[O:44])=[O:43])=[O:23])=[CH:14][CH:15]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 582711903-(2',4',5'-Trifluoro-biphenyl-4-yloxymethyl)-benzoic acid

Produkt 1

HCID 52933064
Cyclopropanesulfonic acid 3-(2',4',5'-trifluoro-biphenyl-4-yloxymethyl)-benzoylamide
Ausbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-benzoic acid (5.0 g, 13.96 mmol) in THF (100 mL) was treated with CDI (3.37 g, 20.78 mmol), heated at 50° C. for 30 min, cooled to room temperature, added cyclopropanesulfonamide (1.86 g, 15.35 mmol) and DBU (4.2 mL, 28.08 mmol) and heated at 60° C. for 17 h. The reaction mixture was cooled to room temperature, treated with aqueous 2N HCl (50 mL), stirred for 10 min, added water (50 mL) and extracted with ethyl acetate (3×100 mL). The organic layers were combined, washed with conc. HCl (20 mL), water (50 mL), 1/1 water/brine (50 mL), brine (50 mL), dried (MgSO4), filtered, concentrated and recrystallized from methanol to give cyclopropanesulfonic acid 3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-benzoylamide (2.58 g, 40.1%) as a white solid. LC-MS (ES) calculated for C23F18F3NO4S, 461.46; found m/z 460 [M−H]−.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperatureheated at 60° C. for 17 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washwashed with conc. HCl (20 mL), water (50 mL), 1/1 water/brine (50 mL), brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-498be165af8f4da6b08c29df830b086e
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08039495B2

Notizen zur Reaktion

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