Glycine tert-butyl ester → Tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate

HRID 1631011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631011
[C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[Cl:10][C:11]1[C:12](Cl)=[N:13][CH:14]=[C:15]([CH:18]=1)[C:16]#[N:17]>>[Cl:10][C:11]1[C:12]([NH:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])=[N:13][CH:14]=[C:15]([C:16]#[N:17])[CH:18]=1

Komponenten

3

Edukt 2

HCID 151417Glycine tert-butyl esterHCID 128784645,6-Dichloropyridine-3-carbonitrile

Produkt 1

HCID 58554110Tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate

Versuchsvorschrift

A mixture of glycine tert-butyl ester (5.3 g, 40.4 mmol), TEA (5.6 mL, 40.4 mmol) and 5,6-dichloronicotinonitrile (Bionet GC-0755, 7.0 g, 40.4 mmol) was prepared and stirred at RT for 24 hours. The reaction mixture was filtered to remove inorganic solids and filtrate was concentrated under reduced pressure. The residue taken up with EtOAc (100 mL) and washed with water (2×100 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. After purification by flash chromatography (silica, pet ether/EtOAc), the title compound was obtained as a white powder. 1H NMR (DMSO-d6, 400 MHz) δ 8.41 (1H, d), 8.15 (1H, d), 7.84 (1H, t), 4.00 (2H, m), 1.38 (9H, s).

Aufarbeitung

  1. customwas prepared
  2. filtrationThe reaction mixture was filtered
  3. customto remove inorganic solids and filtrate
  4. concentrationwas concentrated under reduced pressure
  5. washwashed with water (2×100 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customAfter purification by flash chromatography (silica, pet ether/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-aedf92f5aac3451a867f51e4ad4d0dfb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791142B2

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