Triethylamine → HCID 70161322, compound

HRID 844040Notes

Reaction equation

HRID 844040 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[N:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1.[CH3:26][C:27]([CH3:32])([CH3:31])[C:28](Cl)=[O:29].C(N(CC)CC)C>C(Cl)Cl.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:8]([C:9]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][C:28](=[O:29])[C:27]([CH3:32])([CH3:31])[CH3:26])=[CH:15][CH:14]=3)=[O:10])=[CH:20][CH:21]=[CH:22][N:23]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 22612150HCID 22612150, compound

Product 1

HCID 70161322HCID 70161322, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution 2-(4-Fluoro-phenoxy)-N-(4-hydroxy-benzyl)-nicotinamide (0.050 grams, 0.148 mmole), trimethylacetyl chloride (0.019 grams, 0.163 mmole) and triethyl amine (0.022 grams, 0.222 mmole) in methylene chloride (5 ml) was stirred for 30 minutes. The mixture was diluted with 50 ml 1N sodium hydroxide and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over Na2SO4, filtered and concentrated to give an oil that was purified by chromatography on silica gel eluting with 40% ethyl acetate/hexane. Recrystalization from ethyl acetate/hexane gave a solid (0.043 g). M.P. 91-93° C.; Anal. calcd. for C24H23N2O4F: C, 68.24; H, 5.49; N, 6.63. Found: C, 66.07; H, 5.24; N, 6.42.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas purified by chromatography on silica gel eluting with 40% ethyl acetate/hexane
  8. customRecrystalization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3042eebec47d4adcaded08427901a1b0
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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