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p-Toluenesulfonic acid monohydrate → 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-formyl-N-(2-hydroxy-ethoxy)-benzamide

HRID 2038598
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2038598
[Si]([O:8][CH2:9][CH2:10][O:11][NH:12][C:13](=[O:33])[C:14]1[CH:19]=[C:18]([CH:20]=[O:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=1[F:32])(C(C)(C)C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.O>[F:23][C:16]1[C:15]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])=[C:14]([CH:19]=[C:18]([CH:20]=[O:21])[C:17]=1[F:22])[C:13]([NH:12][O:11][CH2:10][CH2:9][OH:8])=[O:33]
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Komponenten

5

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 23132329N-[2-(t-butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-formyl-benzamide

Produkt 1

HCID 231323883,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-formyl-N-(2-hydroxy-ethoxy)-benzamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

N-[2-(Tert-butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-formyl-benzamide (37.1 g as a crude product containing the desilylated product) prepared in Step E was dissolved in a mixed solvent of tetrahydrofuran (200 ml) and water (16 ml). To this solution, p-toluenesulfonic acid monohydrate (1.76 g, 9.25 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over magnesium sulfate, and evaporated under reduced pressure. The resultant residue was triturated with ethyl acetate to give 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-formyl-N-(2-hydroxy-ethoxy)-benzamide (16.0 g, 72% yield in two steps) as a yellow solid.

Aufarbeitung

  1. customprepared in Step E
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe resultant residue was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3199346b5fd14fcc961b68b9b2a7e02f
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575391B2

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