Potassium Carbonate → 4-[(2-tert-Butoxycarbonylamino-ethyl)-(4-fluoro-benzyl)-amino]-but-2-enoic Acid Methyl Ester

HRID 11706

Reaktionsgleichung

Reaktionsgleichung von HRID 11706
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27]/[CH:28]=[CH:29]/[C:30]([O:32][CH3:33])=[O:31]>CC(C)=O>[CH3:33][O:32][C:30](=[O:31])[CH:29]=[CH:28][CH2:27][N:10]([CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 69655592tert-Butyl (2-((4-fluorobenzyl)amino)ethyl)carbamate

Produkt 1

HCID 696556034-[(2-tert-Butoxycarbonylamino-ethyl)-(4-fluoro-benzyl)-amino]-but-2-enoic Acid Methyl EsterAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

[2-(4-Fluoro-benzylamino)-ethyl]-carbamic acid tert-butyl ester (7.0 g, 26.1 mmol) and potassium carbonate (7.2 g, 52.2 mmol) were stirred in acetone (150 mL). A mixture of methyl 4-bromocrotonate (4.7 g, 26.1 mmol, 3.1 mL) in acetone (50 mL) was added to this solution dropwise using an addition funnel. After 18 h the solution was filtered, concentrated and chromatographed on silica gel to yield the title compound as a yellow oil (8.53 g).

Aufarbeitung

  1. additionwas added to this solution
  2. filtrationAfter 18 h the solution was filtered
  3. concentrationconcentrated
  4. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e4d1881149c74c9fa1f7a0ec43dc4d6d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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