(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 1691949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691949
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-b3676051a7fc4cbcb227de9b5bb6043e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153644B2

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