(1S,2S)-2-(4-{3-fluoro-4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid benzyl ester → (1S,2S)-2-(4-{3-fluoro-4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid

HRID 557791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557791
C([O:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([C:33]3[N:34]=[C:35]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[O:36][C:37]=3[C:38]([F:41])([F:40])[F:39])=[O:32])=[C:26]([F:48])[CH:25]=2)[CH2:20][CH2:19]1)=[O:17])=[O:10])C1C=CC=CC=1>CO.[OH-].[Li+].O>[F:48][C:26]1[CH:25]=[C:24]([N:21]2[CH2:22][CH2:23][N:18]([C:16]([C@H:12]3[CH2:13][CH2:14][CH2:15][C@@H:11]3[C:9]([OH:10])=[O:8])=[O:17])[CH2:19][CH2:20]2)[CH:29]=[CH:28][C:27]=1[NH:30][C:31]([C:33]1[N:34]=[C:35]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:36][C:37]=1[C:38]([F:40])([F:41])[F:39])=[O:32]

Komponenten

5

Edukt 1

HCID 66738142(1S,2S)-2-(4-{3-fluoro-4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid benzyl ester

Produkt 1

HCID 25121473(1S,2S)-2-(4-{3-fluoro-4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3939Lithium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To the solution of (1S,2S)-2-(4-{3-fluoro-4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid benzyl ester in methanol, lithium hydroxide and water were added. The so formed mixture was stirred at 25° C. overnight. Solvent was removed and the residue was resuspended in ethyl acetate and water. Citric acid was added to acidify the mixture. Organic layer was concentrated and the residue was purified on a reverse phase HPLC system to give (1S,2S)-2-(4-{3-fluoro-4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid as a white solid. LCMS calcd for C28H26F4N4O5 (m/e) 574, obsd 575 (M+H).

Aufarbeitung

  1. customThe so formed mixture
  2. customSolvent was removed
  3. additionCitric acid was added
  4. concentrationOrganic layer was concentrated
  5. customthe residue was purified on a reverse phase HPLC system

Quellen und Nachweise

ORD-Eintrag
ord-64376e4e7e1c4c808de9ae1b3d004452
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058299B2

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