Boron tribromide → Octanedioic acid hydroxyamide [4-(2-nitro-phenyl)-thiazol-2-yl]-amide

HRID 243623

Reaktionsgleichung

Reaktionsgleichung von HRID 243623
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][O:26]CC2C=CC=CC=2)=[O:24])[S:13][CH:14]=1)([O-:3])=[O:2].B(Br)(Br)Br>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][OH:26])=[O:24])[S:13][CH:14]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 89972899Octanedioic acid benzyloxy-amide [4-(2-nitro-phenyl)-thiazol-2-yl]-amide

Produkt 1

HCID 25030884Octanedioic acid hydroxyamide [4-(2-nitro-phenyl)-thiazol-2-yl]-amideAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of compound 15 (0.040 g, 0.083 mmol) in methylene chloride (1 mL) was cooled to −30° C. while boron tribromide (0.18 ml) 1M in methylene chloride was added dropwise. After stirring at room temperature for 2 hours, the mixture was cooled to 0° C. and quenched with saturated sodium bicarbonate. The reaction mixture was diluted with ethyl acetate and washed sequentially with saturated NaHCO3, and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to provide a crude residue which was purified by reverse phase HPLC to afford octanedioic acid hydroxyamide [4-(2-nitro-phenyl)-thiazol-2-yl]-amide 17 (0.018 g, 55% yield).

Aufarbeitung

  1. additionwas added dropwise
  2. temperaturethe mixture was cooled to 0° C.
  3. customquenched with saturated sodium bicarbonate
  4. additionThe reaction mixture was diluted with ethyl acetate
  5. washwashed sequentially with saturated NaHCO3, and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto provide a crude residue which
  9. customwas purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8a1e2a1969604e45b6608a012916bb36
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653278B2

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