1-Hydroxybenzotriazole → HCID 86646323, Verbindung

HRID 2356732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356732
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)=[C:11]([CH2:13][C:14]([OH:16])=O)[N:12]=2)=[CH:4][CH:3]=1.Cl.[CH3:23][O:24][NH2:25].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O.C(N(CC)CC)C>[CH3:23][O:24][NH:25][C:14](=[O:16])[CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:9][C:10]=1[C:17]1[CH:21]=[CH:20][S:19][CH:18]=1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 30697874-Oxazoleacetic acid, 2-(p-fluorophenyl)-5-(3-thienyl)-

Produkt 1

HCID 86646323HCID 86646323, VerbindungAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-fluorophenyl)-5-(3-thienyl)oxazol-4-yl acetic acid (100 mg), methoxyamine hydrochloride (37.6 mg), 3-ethyl-1-(3-dimethylaminopropyl)carbodiimide hydrochloride (95 mg), 1-hydroxybenzotriazole (67 mg) and triethylamine (0.14 ml) in N,N-dimethylformamide (3 ml) was stirred at room temperature overnight. Water was added to the reaction mixture, the mixture was extracted with chloroform. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=20:1), and triturated with diethyl ether-hexane to obtain N-methoxy-[2-(4-fluorophenyl)-5-(3-thienyl)oxazol-4-yl]acetamide (75 mg) as colorless powder.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=20:1)
  6. customtriturated with diethyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-417c414fe8d943529fe9a1c4deea8a8e
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759373B2

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