tert-Butanol → (2-Pyridin-2-yl-thiazol-5-yl)-carbamic acid tert-butyl ester

HRID 1260323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260323
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:8][C:9](C(O)=O)=[CH:10][N:11]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])C=CC=CC=1.C([N:34]([CH2:37]C)CC)C.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C:37](=[O:22])[NH:34][C:9]1[S:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:11][CH:10]=1)([CH3:42])([CH3:41])[CH3:40]

Komponenten

5

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 232838552-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acid

Produkt 1

HCID 67299899(2-Pyridin-2-yl-thiazol-5-yl)-carbamic acid tert-butyl ester

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 2-pyridin-2-yl-thiazol-5-carboxylic acid (250 mg, 1.2 mmol) in tert-butanol (4.5 ml) was treated with diphenylphosphoryl azide (0.4 ml, 1.85 mmol) and triethylamine (0.34 ml, 2.4 mmol) and stirred at 90° C. for 5 h. The reaction mixture was extracted with ethyl acetate and the combined organic phases were washed with saturated ammonium acetate solution, water and brine. The final product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as yellow oil (180 mg, 54%). MS: M=278.2 (M+H)+

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe combined organic phases were washed with saturated ammonium acetate solution, water and brine

Quellen und Nachweise

ORD-Eintrag
ord-a3480e7278ba46a181edf2a930f81c39
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470820B2

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