Water → 2-[(4-{2-[(4'-Fluorobiphenyl-4-yl)oxy]-1-methoxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid

HRID 456025Notes

Reaction equation

HRID 456025 reaction equation
[H-].[Na+].C([O:7][C:8](=[O:35])[C:9]([S:12][C:13]1[S:14][CH:15]=[C:16]([CH:18]([OH:34])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[N:17]=1)([CH3:11])[CH3:10])(C)(C)C.[CH3:36]I.O>CN(C=O)C>[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH2:19][CH:18]([C:16]3[N:17]=[C:13]([S:12][C:9]([CH3:10])([CH3:11])[C:8]([OH:7])=[O:35])[S:14][CH:15]=3)[O:34][CH3:36])=[CH:22][CH:23]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 584514012-[(4-{2-[(4'-Fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Product 1

HCID 462360862-[(4-{2-[(4'-Fluorobiphenyl-4-yl)oxy]-1-methoxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% oil suspension, 24 mg) was suspended in DMF (5 mL), and a solution of 2-[(4-{2-[(4′-fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (331 mg) obtained in Example 2-2 in DMF (1.5 mL) was added. After cease of foaming, methyl iodide (0.12 mL) was added, and the mixture was stirred at room temperature for 30 min. Water (20 mL) was added, and the mixture was stirred, extracted with ethyl acetate (50 mL), washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography (Fuji Silysia silica gel BW300 was used. elution solvent: hexane/ethyl acetate-9/1-7/3) to give tert-butyl ester of the title compound (222 mg). By an operation similar to that in Example 2-3 and using the compound, the title compound (177 mg) was obtained.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred
  3. extractionextracted with ethyl acetate (50 mL)
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by column chromatography (Fuji Silysia silica gel BW300 was used. elution solvent: hexane/ethyl acetate-9/1-7/3)

Sources & evidence

ORD record
ord-5c6f9ba0d2f14545999c9ca4b424a389
Source dataset
uspto-grants-2013_07
Patent number
US08497382B2

Reaction notes

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