1-Hydroxybenzotriazole → t-Butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate

HRID 1682687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1682687
[C:1]([C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([OH:14])=O)[O:9][C:6]2=[N:7][CH:8]=1)#[N:2].[NH2:15][C:16]1[CH:30]=[CH:29][C:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:18][CH:17]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:29][CH:30]=3)=[O:14])[O:9][C:6]2=[N:7][CH:8]=1)#[N:2]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 108452775-Cyanofuro[2,3-b]pyridine-2-carboxylic acidHCID 22060435Tert-butyl 2-(4-aminophenoxy)acetate

Produkt 1

HCID 10500772t-Butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Cyanofuro[2,3-b]pyridine-2-carboxylic acid (108 mg, 0.574 mmol) and t-butyl 4-aminophenoxyacetate (141 mg, 0.632 mmol) were dissolved in N,N-dimethylformamide (10 ml) and 1-hydroxy-1H-benzotriazole (85.3 mg, 0.632 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (121 mg, 0.632 mmol) were added. The mixture was stirred at room temperature for 14 hours. Water (100 ml) was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. Low boiling matters were distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to quantitatively give 232 mg of t-butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate as a pale-yellow solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationwere distilled away under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to quantitatively give 232 mg of t-butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate as a pale-yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-2a499049623142aa93c330f498e0c3b8
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05635527

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