Potassium Carbonate → 2-(2-(4-(4-(t-Butoxycarbonylmethoxy)-phenoxy)phenyl)acetylamino)benzoic acid methyl ester

HRID 2181169Notes

Reaction equation

HRID 2181169 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:34])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:33])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1.Br[CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>CN(C=O)C>[CH3:7][O:8][C:9](=[O:34])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:33])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:30][CH:31]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 20602792Methyl 2-(4-(4-hydroxyphenoxy)phenylacetamido)benzoate

Product 1

HCID 697468002-(2-(4-(4-(t-Butoxycarbonylmethoxy)-phenoxy)phenyl)acetylamino)benzoic acid methyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (162 mg) was added to 221 mg of 2-(2-(4-(4-hydroxyphenyloxy)phenyl)acetylamino)benzoic acid methyl ester obtained by the Reference Example 24, the mixture was suspended in dried DMF (5 ml), t-butyl bromoacetate (130 μl) was added little by little to the suspension at room temperature, and the mixture was stirred as it is over a night at room temperature. After completing the reaction, DMF was distilled out under reduced pressure and the product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of potassium bisulfate and dried with anhydrous magnesium sulfate. After removing the solvent by distillation, the residue was purified by silica gel column chromatography (developing liquid: hexane:ethyl acetate 4:1 to 1:1) to obtain 174 mg of the subject compound. The 1H-NMR of the compound was consistent with the above structure.

Workup

  1. customobtained by the Reference Example 24
  2. waitis over a night at room temperature
  3. distillationwas distilled out under reduced pressure
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous solution of potassium bisulfate
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customAfter removing the solvent
  8. distillationby distillation
  9. customthe residue was purified by silica gel column chromatography (developing liquid: hexane:ethyl acetate 4:1 to 1:1)

Sources & evidence

ORD record
ord-7a4c8d34e18a4135be107bb600387811
Source dataset
uspto-grants-2005_05
Patent number
US06890932B2

Reaction notes

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