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

HRID 557778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557778
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[N:21]=[C:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:23][C:24]=3[C:25]([F:28])([F:27])[F:26])=[O:19])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[C:29]1([C:22]2[O:23][C:24]([C:25]([F:26])([F:27])[F:28])=[C:20]([C:18]([NH:17][C:14]3[CH:13]=[CH:12][C:11]([N:8]4[CH2:7][CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]4)=[CH:16][CH:15]=3)=[O:19])[N:21]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 576520321-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid methyl ester

Produkt 1

HCID 576521231-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acidAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The above 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid methyl ester (470 mg, 1 mmol) was dissolved in a mixture of methanol (7 mL) and THF (2 mL). To this solution was added 1N sodium hydroxide solution (3 mL). The mixture was stirred at room temperature for 4 hrs until all starting material was consumed. Solvents were evaporated and the residue was diluted with water (8 mL). The solution was filtered and the filtrate was acidified with 1N hydrochloric acid (3.5 mL). The yellow precipitate was filtered and dried in the air to give 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid (395 mg). 1H-NMR is consistent with the desired structure. LC-MS indicated a single peak (Rf=3.23 min). LRMS for C23H20F3N3O4 (m/e) calcd 459.14, obsd 460.2 (M+1).

Aufarbeitung

  1. customwas consumed
  2. customSolvents were evaporated
  3. additionthe residue was diluted with water (8 mL)
  4. filtrationThe solution was filtered
  5. filtrationThe yellow precipitate was filtered
  6. customdried in the air

Quellen und Nachweise

ORD-Eintrag
ord-5d4f95918fee4b3594c6f7e170adf721
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058299B2

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