Sodium Bicarbonate → HCID 57594302, Verbindung

HRID 730335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730335
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1)=O.[NH2:24][C:25]1[C:30]([CH:31]([OH:33])[CH3:32])=[CH:29][CH:28]=[CH:27][N:26]=1.C(=O)(O)[O-].[Na+]>C(O)(C)C>[OH:15][CH2:14][CH2:13][C@@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:24]=[C:25]3[C:30]([CH:31]([OH:33])[CH3:32])=[CH:29][CH:28]=[CH:27][N:26]3[CH:2]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 447548961-(2-Aminopyridin-3-yl)ethanolHCID 575947321,1-dimethylethyl ((1S)-1-{[4-(bromoacetyl)phenyl]methyl}-3-hydroxypropyl)carbamate

Produkt 1

HCID 57594302HCID 57594302, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 1,1-dimethylethyl ((1S)-1-{[4-(bromoacetyl)phenyl]methyl}-3-hydroxypropyl)carbamate (1.00 g, 2.59 mmol), 1-(2-amino-3-pyridinyl)ethanol (0.358 g, 2.59 mmol), and solid sodium bicarbonate (0.272 g, 3.24 mmol) in isopropanol (25 mL) was heated at reflux for 3.5 h. and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with water and brine, dried (Na2SO4), and concentrated. The resulting pale yellow solid was used in the next reaction without further purification. MS(ES+) m/e 426 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 h.
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe resulting pale yellow solid was used in the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-f0a63abdee7b4e7380d87c356dbc8412
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582668B2

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