Potassium Carbonate → Methyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)-phenoxy)methyl)benzoate

HRID 332691Notes

Reaction equation

HRID 332691 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7](C1C=CC=C(O)C=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1.[C:35](=[O:38])([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:5][C:6]([NH:7][CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:10]1[CH:11]=[C:35]([CH:13]=[CH:14][CH:9]=1)[O:38][CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)=[O:22])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 86676908Tert-butyl(3-hydroxyphenyl)(phenyl)methylcarbamate

Product 1

HCID 71093072Methyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)-phenoxy)methyl)benzoateYield 135.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl(3-hydroxyphenyl)(phenyl)methylcarbamate (3.20 g, 10.7 mmol), methyl 4-(bromomethyl)benzoate (2.70 g, 11.8 mmol), and potassium carbonate (2.20 g, 16.1 mmol) in acetonitrile (54 mL) was stirred at room temperature for 16 hours. The reaction mixture was concentrated at reduced pressure, and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with further ethyl acetate, and the combined organic extracts combined, dried with anhydrous magnesium sulfate, filtered and the solvent evaporated at reduced pressure. The residue was re-crystallised from ethyl acetate and iso-hexane to afford the title compound (3.25 g, 68%).

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with further ethyl acetate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated at reduced pressure
  7. customThe residue was re-crystallised from ethyl acetate and iso-hexane

Sources & evidence

ORD record
ord-635e077da9b540719b63fc238b1a3fda
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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