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Cesium carbonate → 3-Benzyloxycarbonylamino 6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 413436
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 413436
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:10]([O:17][C:18]([NH:20][C:21]1[C:22](=[O:28])[NH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[CH2:10]([O:17][C:18]([NH:20][C:21]1[C:22](=[O:28])[N:23]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:24]([CH3:27])=[CH:25][CH:26]=1)=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 100838403-Benzyloxycarbonylamino-6-methyl-2-pyridone

Produkt 1

HCID 102486933-Benzyloxycarbonylamino 6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinoneAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

tert-Butyl bromoacetate (3.9 g, 20 mmol) was added to a stirred suspension of 3-benzyloxycarbonylamino-6-methyl-2-pyridinone (5.15 g, 20 mmol), as prepared in the preceding step, and Cs2CO3 (6.5 g, 20 mmol) in N,N-dimethylformamide (50 mL) and stirred at 40° C. overnight. The solid was removed by filtration and the filtrate concentrated under high vacuum. The residue was dissolved in ethyl acetate (150 mL), washed with water (2×50 mL), brine (50 mL), dried over Na2SO4 and concentrated in vacuo. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography (25% ethyl acetate in hexane) to give the title compound as a white crystalline solid (4.2 g, 56%). 1H-NMR (300 MHz, CDCl3) δ7.95 (d, J=7.3 Hz, 1H), 7.76 (s, 1H), 7.37 (m, 5H), 6.09 (d, J=7.6 Hz, 1H), 5.19 (s, 2H), 4.75 (s, 2H), 2.32 (s, 3H), 1.47 (s, 9H).

Aufarbeitung

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate concentrated under high vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  4. washwashed with water (2×50 mL), brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customAfter evaporating the solvent in vacuo
  8. customthe residue was purified by flash column chromatography (25% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0fb5643b6b77442da815da33b25399e5
Quelldatensatz
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06566379B1

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