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4-Fluorophenol → HCID 59363813, 화합물

HRID 1430639
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HRID 1430639 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][CH2:15][O:16]S(C)(=O)=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][CH2:15][O:16][C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)[N:13]=1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

4

반응물 2

HCID 97324-FluorophenolHCID 59363822HCID 59363822, 화합물

생성물 1

HCID 59363813HCID 59363813, 화합물수율 42%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a mixture of Methanesulfonic acid 2-(2-tert-butoxycarbonylamino-thiazol-4-yl)-ethyl ester (6.0 g, 18 mmol) and 4-fluoro phenol (5.21 g, 46 mmol) in Toluene (60 ml) K2Co3 (7.7 g, 55 mmol) was added and heated at 80° C. for 18 h. The reaction mixture was filtered to remove solid residues, washed with ethyl acetate (50 ml) and combined organic layer washed with brine (20 ml) dried over Na2SO4. Solvent was removed under reduced pressure, crude product was purified by column chromatography using 1:10 EtOAC and Hexanes to obtain {4-[2-(4-Fluoro-phenoxy)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (2.56 g, 40%). 1H NMR (400 MHz, CDCl3): 1.53 (s, 9H), 3.09 (t, J=6.4 Hz, 2H), 4.20 (t, J=6.4 Hz, 2H), 6.21 (s, 1H), 6.811-6.84 (m, 2H), 6.95 (t, J=8.8 Hz, 2H). 8.28 (brs, 1H). MS (EI) m/z: 338.89 (M+1).

후처리

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. customto remove solid residues
  4. washwashed with ethyl acetate (50 ml)
  5. washwashed with brine (20 ml)
  6. dry with materialdried over Na2SO4
  7. customSolvent was removed under reduced pressure, crude product
  8. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-9e28297969364601963872d14b42cc1c
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08940900B2

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