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Tetrahydrofuran → 2-(3-{(2E)-3-[4-(tert-Butyl)phenyl]prop-2-enoylamino}phenoxy)acetic acid

HRID 2105564
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2105564
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.Br[CH2:29][C:30]([O:32]C(C)(C)C)=[O:31]>[OH-].[Na+]>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=2)[O:22][CH2:29][C:30]([OH:32])=[O:31])=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 79177tert-Butyl bromoacetateHCID 10214883(2E)-3-[4-(tert-Butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide

Produkt 1

HCID 101723092-(3-{(2E)-3-[4-(tert-Butyl)phenyl]prop-2-enoylamino}phenoxy)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a round-bottomed flask equipped with magnetic stirring was added (2E)-3-[4-(tert-butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide, Example 23, (120 mg, 0.407 mmol), THF (10 mL), tert-butyl bromoacetate (60 uL, 0.407 mmol, Aldrich) and 5 N NaOH (10 mL). The reaction mixture was stirred at 25° C. overnight. The mixture was extracted with EtOAc (20 mL), the organic extract washed with water (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was treated with trifluoroacetic acid (10 mL), stirred at 25° C. for 2 h, then concentrated in vacuo. Purification by silica gel chromatography (1:2 hexane:EtOAc) provided the title product as an off-white solid. MP 166-172° C. MS (ESI, pos. ion) m/z: 354 (M+1).

Aufarbeitung

  1. customTo a round-bottomed flask equipped
  2. stirringThe reaction mixture was stirred at 25° C. overnight
  3. extractionThe mixture was extracted with EtOAc (20 mL)
  4. extractionthe organic extract
  5. washwashed with water (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionThe resulting residue was treated with trifluoroacetic acid (10 mL)
  10. stirringstirred at 25° C. for 2 h
  11. concentrationconcentrated in vacuo
  12. customPurification by silica gel chromatography (1:2 hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-d09cfde221e54bd4bca76479c870a090
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07579347B2

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