tert-Butanol → Ethyl 6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

HRID 2244413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244413
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](C(O)=O)[N:7]=1)=[O:5])[CH3:2].C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:17][C:20]([O:43][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:29])[N:7]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 35944446-(Ethoxycarbonyl)picolinic acid

Produkt 1

HCID 19349079Ethyl 6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of pyridine-2,6-dicarboxylic acid monoethyl ester (1.00 g, 5.12 mmol), triethylamine (1.04 g, 10.24 mmol), diphenylphosphoryl azide (DPPA) (1.93 g, 7.02 mmol) and tert-butanol (3.00 ml) in toluene (30.00 ml) was warmed at 100° C. for 20 h. The mixture was then cooled at room temperature, diluted with ethyl acetate and washed with saturated sodium bicarbonate and brine. The organic layer was then dried over sodium sulphate and evaporated. The residue was purified by flash chromatography to yield 6-tert-butoxycarbonylamino-pyridine-2-carboxylic acid ethyl ester (1.06 g, 78%) as a viscous orange oil, MS (ISP): m/e=267.3 (M+H+).

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate and brine
  2. dry with materialThe organic layer was then dried over sodium sulphate
  3. customevaporated
  4. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dc32e2909aef4fe6adb1df949762e70f
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678815B2

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