4-Fluorophenol → HCID 59363813, compound

HRID 1430639Notes

Reaction equation

HRID 1430639 reaction equation
[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]

Participants

4

Reactant 2

HCID 97324-FluorophenolHCID 59363822HCID 59363822, compound

Product 1

HCID 59363813HCID 59363813, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9e28297969364601963872d14b42cc1c
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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