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Sodium Hydroxide → 1-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid

HRID 1510269
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1510269
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]3[N:22]=[C:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:24][C:25]=3[C:26]([F:29])([F:28])[F:27])=[O:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[C:30]1([C:23]2[O:24][C:25]([C:26]([F:27])([F:28])[F:29])=[C:21]([C:19]([NH:18][C:15]3[CH:14]=[CH:13][C:12]([N:9]4[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]4)=[CH:17][CH:16]=3)=[O:20])[N:22]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
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Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 576521271-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid ethyl ester

Produkt 1

HCID 576521231-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acidAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid ethyl ester (1.1 g, 2.3 mmol) in 20 mL of MeOH was treated with 2.8 mL (5.6 mmol) of 2 N NaOH, and the reaction mixture was stirred at room temperature overnight. The resulting mixture was then concentrated to remove most of the MeOH solvent. The residue was then neutralized with concentrated HCl. A white precipitate formed. The product was then collected by filtration, washed with water, triturated with ether, and dried to furnish 0.82 g of 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid. This material was used in the next step without further purification.

Aufarbeitung

  1. concentrationThe resulting mixture was then concentrated
  2. customto remove most of the MeOH solvent
  3. customA white precipitate formed
  4. filtrationThe product was then collected by filtration
  5. washwashed with water
  6. customtriturated with ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f11f89c525524c439b48764bbe76f897
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08211914B2

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