Trifluoroacetic acid → N-{4-[2-(4-Methoxyphenyl)ethoxy]benzoyl}glycine

HRID 1099540

Reaction equation

HRID 1099540 reaction equation
C(P(=CC#N)(CCCC)CCCC)CCC.C([O:21][C:22](=[O:34])[CH2:23][NH:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)(C)(C)C.[CH3:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44]O)=[CH:39][CH:38]=1.FC(F)(F)C(O)=O>ClCCl.O.C1(C)C=CC=CC=1>[CH3:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][O:32][C:29]2[CH:28]=[CH:27][C:26]([C:25]([NH:24][CH2:23][C:22]([OH:21])=[O:34])=[O:33])=[CH:31][CH:30]=2)=[CH:39][CH:38]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 697054-Methoxyphenethyl alcoholHCID 4622928CyanomethylenetributylphosphoraneHCID 10682169N-(4-Hydroxybenzoyl)glycine tert-butyl ester

Product 1

HCID 66812093N-{4-[2-(4-Methoxyphenyl)ethoxy]benzoyl}glycineYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

(Tributyl phosphoranylidene)acetonitrile (428 μL, 1.50 mmol) was added to a solution of toluene (7 mL) containing N-(4-hydroxybenzoyl)glycine tert-butyl ester (264 mg, 1.05 mmol) prepared in Example 1 (1a) and 2-(4-methoxyphenyl)ethanol (176 mg, 1.16 mmol). The mixture was stirred at 100° C. for 3.5 hours, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate, 6:1, 4:1, and 3:1, v/v) to give an oily substance (358 mg). To a solution of dichloromethane (1 mL) containing this oily substance (358 mg, 0.929 mmol), trifluoroacetic acid (0.5 mL) was added. The mixture was stirred at room temperature for 1 hour, and then the solvent was evaporated. Diisopropyl ether was added to the resulting residue to suspend it. The produced precipitate was collected by filtration and was washed with diisopropyl ether to give 248 mg of the title compound (colorless crystalline solid, yield: 72%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen, the solvent was evaporated
  5. customThe resulting residue was purified by silica gel column chromatography (hexane to hexane
  6. customethyl acetate, 6:1, 4:1, and 3:1, v/v) to give an oily substance (358 mg)
  7. additionwas added
  8. stirringThe mixture was stirred at room temperature for 1 hour
  9. customthe solvent was evaporated
  10. additionDiisopropyl ether was added to the resulting residue
  11. filtrationThe produced precipitate was collected by filtration
  12. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-c2b5635cc9c646f49e785df05fafb49b
Source dataset
uspto-grants-2012_03
Patent number
US08143446B2

Linked notes

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