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Tetrahydrofuran → Di-tert-butyl ([(4-{2-[2-(acetylamino)-5-bromo-1,3-thiazol-4-yl]ethyl}phenyl)amino]methylidene}biscarbamate

HRID 2117871
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2117871
[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]2[N:27]=[C:28]([NH:31][C:32](=[O:34])[CH3:33])[S:29][CH:30]=2)=[CH:20][CH:19]=1)[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[Br:41]N1C(=O)CCC1=O>CO>[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][C:26]2[N:27]=[C:28]([NH:31][C:32](=[O:34])[CH3:33])[S:29][C:30]=2[Br:41])=[CH:22][CH:23]=1)[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 86595595Di-tert-butyl {[(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)amino]methylidene}biscarbamate

Produkt 1

HCID 86595594Di-tert-butyl ([(4-{2-[2-(acetylamino)-5-bromo-1,3-thiazol-4-yl]ethyl}phenyl)amino]methylidene}biscarbamateAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

Di-tert-butyl{[(4-(2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl)phenyl)amino]methylidene}biscarbamate (310 mg) prepared in a similar manner according to Step 5 of the following Production Example 18 was dissolved in methanol (6 ml) and tetrahydrofuran (3 ml) under nitrogen atmosphere. Then N-bromosuccinimide (164 mg) was added to the solution at 0° C. The reaction mixture was stirred at room temperature for 4 hours, and concentrated in vacuo. Chloroform and saturated sodium hydrogen carbonate solution were added to the residue. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (2:1) as an eluent to give di-tert-butyl{[(4-{2-[2-(acetylamino)-5-bromo-1,3-thiazol-4-yl]ethyl}phenyl)amino]-methylidene)biscarbamate (271.4 mg) as a colorless amorphous substance.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionChloroform and saturated sodium hydrogen carbonate solution were added to the residue
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (2:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-64e6db5f51ec499b9ea80d650f61fab8
Quelldatensatz
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07442715B2

Notizen zur Reaktion

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