Diisopropylethylamine → Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-isopropyl-1,3-thiazole-5-carboxylate

HRID 43882

Reaktionsgleichung

Reaktionsgleichung von HRID 43882
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:14]1[S:15][C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]([CH:19]([CH3:21])[CH3:20])[N:18]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][N:11]([C:14]2[S:15][C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]([CH:19]([CH3:20])[CH3:21])[N:18]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 9943530Ethyl 2-bromo-4-isopropylthiazole-5-carboxylate

Produkt 1

HCID 67548483Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-isopropyl-1,3-thiazole-5-carboxylateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-tert-butoxycarbonylaminoazetidine (136 mg, 0.79 mmol), ethyl 2-bromo-4-isopropyl-1,3-thiazole-5-carboxylate obtained in Example (23b) (200 mg, 0.72 mmol) and diisopropylethylamine (0.25 mL, 1.44 mmol) in DMF (8 mL) was stirred at 90° C. for 11 hours. The reaction solution was diluted with ethyl acetate, and then the mixture was washed with 10% saline and dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1) to obtain 175 mg of the title compound as a white solid (66%).

Aufarbeitung

  1. washthe mixture was washed with 10% saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-99c2381ecc4b4614b08aeb3b6ae8d7af
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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