Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate → 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclo-pentanecarboxylic acid

HRID 340793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340793
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:26]([F:27])=[CH:25][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:19][CH2:18][CH:17]([C:20]([O:22]CC)=[O:21])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:28])=[CH:3][CH:2]=1.O([Si](C)(C)C)[K]>C1COCC1.CCOC(C)=O>[C:1]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:26]([F:27])=[CH:25][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=[O:21])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:28])=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 67406155Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylateHCID 178504318HCID 178504318, Verbindung

Produkt 1

HCID 533723783-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclo-pentanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate (0.039 g, 0.084 mmol) was dissolved in 1 mL of THF and treated with KOTMS (0.032 g, 0.253 mmol). The reaction mixture was stirred overnight at ambient temperature, and then diluted with EtOAc and washed with 2 N HCl. The layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to afford the title compound as a white solid. LCMS: calculated for C25H20F2N2O3 434.43, observed m/e 434.9 (M+H)+ (Rt 2.24/4 min). 1H NMR (500 MHz, d6-DMSO): δ7.77 (d, 2H), 7.73 (d, 2H), 7.56-7.46 (m, 4H), 7.39 (m, 111), 7.14 (d, 1H), 5.50 (m, 1H), 2.95 (m, 1H), 2.20-1.80 (m, 6H).

Aufarbeitung

  1. washwashed with 2 N HCl
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-be5e999678c0489b993412ddfd601f19
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895596B2

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