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Water → (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-carboxy-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid

HRID 1779150
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HRID 1779150 반응식
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([F:48])([F:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].O.C(N(CC)CC)C.[Br-].[Li+]>C(#N)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([F:47])([F:48])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 82050Lithium BromideHCID 60150052(E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid

생성물 1

HCID 73291867(E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-carboxy-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid
수율 54%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

(E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid (No. 5514403, 100 mg, 0.142 mmol) was dissolved in acetonitrile (1.0 mL), and subsequently water (0.005 mL, 0.278 mmol), triethylamine (0.118 mL, 0.847 mmol) and anhydrous lithium bromide (244 mg, 2.81 mmol) were sequentially added at room temperature. The mixture was stirred at 50° C. for 11.5 hours. After cooling the reaction solution to room temperature, a preparative HPLC was performed to obtain 51.1 mg of the title compound (0.07629 mmol, 54% yield).

후처리

  1. temperatureAfter cooling the reaction solution to room temperature

출처 및 근거

ORD 기록
ord-fc5fd11b03e9439b8f34bce2023be719
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266853B2

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