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Trifluoromethanesulfonic acid → (6-((Methylsulfonyl)oxy)-2-(4-((methylsulfonyl)oxy)phenyl)benzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-, hydrochloride

HRID 1649605
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Reaktionsgleichung

Reaktionsgleichung von HRID 1649605
[ClH:1].[N:2]1([CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:20][S:21]([O:24][C:25]1[CH:26]=[CH:27][C:28]2[CH:32]=[C:31]([C:33]3[CH:38]=[CH:37][C:36]([O:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:35][CH:34]=3)[S:30][C:29]=2[CH:44]=1)(=[O:23])=[O:22].FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>CO.ClCCl>[ClH:1].[CH3:20][S:21]([O:24][C:25]1[CH:26]=[CH:27][C:28]2[C:32]([C:15](=[O:17])[C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][N:2]4[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]4)=[CH:19][CH:18]=3)=[C:31]([C:33]3[CH:34]=[CH:35][C:36]([O:39][S:40]([CH3:43])(=[O:41])=[O:42])=[CH:37][CH:38]=3)[S:30][C:29]=2[CH:44]=1)(=[O:22])=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 57438354-(2-Piperidinoethoxy)benzoic acid hydrochlorideHCID 132860414-(6-(Methylsulfonyloxy)benzo(b)thiophen-2-yl)phenyl methanesulfonate

Produkt 1

HCID 19603580(6-((Methylsulfonyl)oxy)-2-(4-((methylsulfonyl)oxy)phenyl)benzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-, hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The acid chloride was formed from 2.0 g. of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, as described in Example 1, and was combined with 2 g. of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-benzo[b]thiophene in 50 ml. of dichloromethane. A 2.4 g. portion of trifluoromethanesulfonic acid was added, and the mixture was stirred overnight under reflux. The reaction mixture was then poured over ice and sodium bicarbonate solution, and the organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum to a yellow foam, which was treated with excess 3% hydrogen chloride in anhydrous methanol. The mixture was evaporated to dryness under vacuum to obtain a white foam which was dissolved in 18 ml. of boiling methanol. The solution was cooled to obtain 3.1 g. of the desired product, m.p. 128°-130° C., which was identified by nmr analysis.

Aufarbeitung

  1. temperatureunder reflux
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum to a yellow foam, which
  5. additionwas treated with excess 3% hydrogen chloride in anhydrous methanol
  6. customThe mixture was evaporated to dryness under vacuum
  7. customto obtain a white foam which
  8. dissolutionwas dissolved in 18 ml
  9. temperatureThe solution was cooled
  10. customto obtain 3.1 g

Quellen und Nachweise

ORD-Eintrag
ord-e24c749255e14ba39c6cc3c27173394f
Quelldatensatz
uspto-grants-1983_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04418068

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