Sodium Hydroxide → 6-[[2-Methoxy-1-phenyl-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

HRID 460532

Reaktionsgleichung

Reaktionsgleichung von HRID 460532
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1.[CH3:25][O:26][C:27](OC)(OC)OC.[OH-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]2[N:16]=[C:25]([O:26][CH3:27])[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]=2[CH:11]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 74613Tetramethyl orthocarbonateHCID 120430856-(3-Phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester

Produkt 1

HCID 99692876-[[2-Methoxy-1-phenyl-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

200 mg of 6-(3-phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester was mixed with 0.12 ml of tetramethylorthocarbonate and 40 μl of acetic acid, and the mixture was heated for 4 hours to 80° C. After cooling, it was mixed with 1N sodium hydroxide solution, extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 104 mg was obtained.

Aufarbeitung

  1. temperaturethe mixture was heated for 4 hours to 80° C
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washthe combined organic phases were washed with saturated sodium chloride solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue was purified by column chromatography on silica gel
  8. custom104 mg was obtained

Quellen und Nachweise

ORD-Eintrag
ord-cc4cad887e00467faafc24f3bc557a5f
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196202B2

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