(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 1641869노트

반응식

HRID 1641869 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 3939Lithium Hydroxide용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9fec69529e7d43298273c30a19981ad4
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08115011B2

반응 노트

불러오는 중…