(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 1641869ノート

反応式

HRID 1641869 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 3939Lithium Hydroxide溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9fec69529e7d43298273c30a19981ad4
出典データセット
uspto-grants-2012_02
特許番号
US08115011B2

反応ノート

読み込み中…