Citric Acid → Tert-butyl 2-(2-(benzyloxy)-5-phenoxybenzamido)-4-phenylbenzoate

HRID 454632Notes

Reaction equation

HRID 454632 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C.[CH2:27]([O:34][C:35]1[CH:62]=[CH:61][C:60](I)=[CH:59][C:36]=1[C:37]([NH:39][C:40]1[CH:52]=[C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:50]=[CH:49][C:41]=1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:38])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cu]Cl.C(OCC)(=O)C.CN1CCCC1=O>[CH2:27]([O:34][C:35]1[CH:62]=[CH:61][C:60]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:59][C:36]=1[C:37]([NH:39][C:40]1[CH:52]=[C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:50]=[CH:49][C:41]=1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:38])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

9

Reactant 5

HCID 311Citric AcidHCID 996PhenolHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedione2×HCID 66990274Tert-butyl 2-(2-(benzyloxy)-5-iodobenzamido)-4-phenylbenzoate

Product 1

HCID 66991357Tert-butyl 2-(2-(benzyloxy)-5-phenoxybenzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalyst2×HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

Phenol (0.029 mL), cesium carbonate (0.11 g), 2,2,6,6-tetramethylheptane-3,5-dione (3.4 μL), and copper(I) chloride (8.2 mg) were added to a 1-methyl-2-pyrrolidone (0.60 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-iodobenzamido)-4-phenylbenzoate (0.10 g), followed by stirring under a nitrogen atmosphere at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, and then 2,2,6,6-tetramethylheptane-3,5-dione (3.4 μL) and copper(I) chloride (8.2 mg) were added thereto, followed by stirring under a nitrogen atmosphere at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-95% hexane/ethyl acetate] to obtain 0.049 g of tert-butyl 2-(2-(benzyloxy)-5-phenoxybenzamido)-4-phenylbenzoate (0.049 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring under a nitrogen atmosphere at 100° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-95% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-99ab54e73e0a471ab7c84f5286b95025
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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