Hydrochloric Acid → 3-Methoxybenzoic Acid

HRID 130496

Reaktionsgleichung

Reaktionsgleichung von HRID 130496
FC1C=C(C2C=CC=CC=2S(C)(=O)=O)C=CC=1NC(C1N([C:16]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:17]=2[C:18]([OH:20])=[O:19])N=C(C(F)(F)F)C=1)=O.COC(=O)C1C=C(OC)C=CC=1N1C(C(=O)NC2C=CC(C3C=CC=CC=3S(C)(=O)=O)=CC=2F)=CC(C(F)(F)F)=N1.[OH-].[Na+].Cl>CO.O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][CH:16]=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 586301122-[5-(3-Fluoro-2'-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxy-benzoic acidHCID 586302552-[5-(3-Fluoro-2'-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxybenzoic acid methyl ester

Produkt 1

HCID 114613-Methoxybenzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Part D: Preparation of 2-[5-(3-Fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxy-benzoic acid. 2-[5-(3-Fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxybenzoic acid methyl ester (1.70 g, 2.80 mmol) was dissolved in methanol (22 mL), 1N sodium hydroxide (5.8 mL) was added, and the solution refluxed for 6 hours. The reaction was cooled to ambient temperature and diluted with water (30 mL). 3N hydrochloric acid was added to adjust the pH to 2, and the resulting precipitate collected by filtration. The solid was dried under vacuum in a desiccator to give 1.45 g (86%) of (3-fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxy-benzoic acid. 1H NMR (CD3OD) δ 8.12 (dd, J=1.5, 8.1 Hz, 1H), 7.86 (t, J=8.4 Hz, 1H), 7.70 (dt, J=1.5, 7.7 Hz, 1H), 7.61 (dt, J=1.5, 7.7 Hz, 1H), 7.37 (m, 3H), 7.25 (dd, J=2.2, 11.7 Hz, 1H) 7.16 (m, 3H) 3.87 (s, 3H), 2.67 (s, 3H).

Aufarbeitung

  1. temperaturethe solution refluxed for 6 hours
  2. filtrationthe resulting precipitate collected by filtration
  3. customThe solid was dried under vacuum in a desiccator

Quellen und Nachweise

ORD-Eintrag
ord-cae83c570c1247afa1f0b18e7dd23a20
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381732B2

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