Hydrochloric Acid → 1-carboxymethyl-5-(3-fluoro-5-trifluoromethyl-benzyloxy)-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1242865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1242865
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([F:23])[CH:14]=2)[N:8]([CH2:24][C:25]([O:27]CC)=[O:26])[N:7]=1)=[O:5])[CH3:2].[Li+].[OH-].Cl>O1CCCC1.O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]([F:20])([F:22])[F:21])[CH:16]=[C:15]([F:23])[CH:14]=2)[N:8]([CH2:24][C:25]([OH:27])=[O:26])[N:7]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 210629671-ethoxycarbonylmethyl-5-(3-fluoro-5-trifluoromethyl-benzyloxy)-1H-pyrazole-3-carboxylic acid ethyl ester

Produkt 1

HCID 693640081-carboxymethyl-5-(3-fluoro-5-trifluoromethyl-benzyloxy)-1H-pyrazole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice cold solution of 1-ethoxycarbonylmethyl-5-(3-fluoro-5-trifluoromethyl-benzyloxy)-1H-pyrazole-3-carboxylic acid ethyl ester (2) in 1 mL of tetrahydrofuran and 0.2 mL of water was added 0.21 mL (0.21 mmol) of 1 M LiOH solution, and the mixture was allowed to warm up to rt for 2 h. The reaction mixture was then acidified with 0.25 mL (0.25 mmol) of 1 M HCl solution, and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, and concentrated to give 58.5 mg (0.150 mmol) of 1-carboxymethyl-5-(3-fluoro-5-trifluoromethyl-benzyloxy)-1H-pyrazole-3-carboxylic acid ethyl ester (3) as crude product.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-27f638362101404e9c508d35130b3bf9
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115749B2

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