Chloroacetaldehyde → HCID 57906525, Verbindung

HRID 420489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420489
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH2:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].Cl[CH2:24][CH:25]=O>>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[C:14]([Br:15])=[CH:13][N:12]2[CH:24]=[CH:25][N:16]=[C:11]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 57906440HCID 57906440, Verbindung

Produkt 1

HCID 57906525HCID 57906525, VerbindungAusbeute 79 %

Versuchsvorschrift

A mixture of (2-amino-5-bromo-pyridin-4-ylmethyl)-carbamic acid tert-butyl ester (1.0 g, 3.3 mmol), NaHCO3 (474 mg, 5.6 mmol) and chloracetaldehyde (2.2 mL, 15.0 mmol) was vigorously stirred and refluxed for 14 h. The reaction mixture was cooled to RT, concentrated under vacuum and the remaining residue was suspended in DCM and brine. The aqueous layer was separated and extracted with DCM (5×), and the combined organic fractions were dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/DCM/TBME 10:10:1→1:1:18) to yield the title compound (860 mg, 2.6 mmol, 79%) as a pale yellow solid. MS: 327 [M+1]+; HPLC: AtRet=1.07; TLC: RF 0.16 (hexane/DCM/TBME 1:1:2).

Aufarbeitung

  1. temperaturerefluxed for 14 h
  2. concentrationconcentrated under vacuum
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM (5×)
  5. dry with materialthe combined organic fractions were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/DCM/TBME 10:10:1→1:1:18)

Quellen und Nachweise

ORD-Eintrag
ord-62a3cb6af6e6429f8177b787841b741e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097617B2

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