Water → 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid monomethyl ester

HRID 1747334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747334
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH:5]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:20]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=3[S:22][CH:23]=2)[C:10]1=[O:29])[CH2:6][CH2:7][OH:8].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:32].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH:5]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:20]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=3[S:22][CH:23]=2)[C:10]1=[O:29])[CH2:6][C:7]([OH:32])=[O:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 59497341HCID 59497341, Verbindung

Produkt 1

HCID 251235483-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid monomethyl esterAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Hydroxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]pentanoic acid methyl ester (70 mg, 0.17 mmol) is dissolved in DMF (1.5 mL) at room temperature and pyridinium dichromate (250 mg, 0.66 mmol) is added into it. The mixture is stirred for 20 hr and water (25 mL) is added. The pH of the solution is adjusted to pH 5 by adding acetic acids and the mixture is extracted with EtOAc (3×50 mL). The organic layers are combined, dried and concentrated to give crude product. Purification by preparative TLC using 80% EtOAc in Hexanes with 1% acetic acid affords 48 mg (66%) of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid monomethyl ester. LCMS (ESMS): m/z 439.17 (M+H+).

Aufarbeitung

  1. extractionthe mixture is extracted with EtOAc (3×50 mL)
  2. customdried
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-ec214586ae274e9ebbaba02ea9bc8692
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

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