Sodium Hydroxide → Rac.-2-((diphenylmethylene)amino]-3-[4-[(1,1-dimethylethoxy) carbonyl]phenyl]propanoic acid benzyl ester

HRID 1721234Notes

Reaction equation

HRID 1721234 reaction equation
S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].[CH2:42]([O:49][C:50](=[O:66])[CH2:51][N:52]=[C:53]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Br[CH2:68][C:69]1[CH:81]=[CH:80][C:72]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])=[CH:71][CH:70]=1>ClCCl.CCOCC>[CH2:42]([O:49][C:50](=[O:66])[CH:51]([N:52]=[C:53]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[CH2:68][C:69]1[CH:70]=[CH:71][C:72]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])=[CH:80][CH:81]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 11433187Bis(tetrabutylammonium) sulphateHCID 11782449Diphenylmethylene-Glycine benzyl ester

Product 1

HCID 14888672Rac.-2-((diphenylmethylene)amino]-3-[4-[(1,1-dimethylethoxy) carbonyl]phenyl]propanoic acid benzyl esterYield 36%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Tetrabutyl ammonium sulfate (3.0 g, 9 mmol) was added to a biphasic mixture consisting of 10% aqueous sodium hydroxide (75 mL), 2-[(diphenylmethylene)amino]acetic acid benzyl ester (3.05 g, 9.3 mmol) and 1,1-dimethylethyl 4-bromomethylbenzoate (3.0 g, 9 mmol) in dichloromethane (58 mL). After several hours of vigorous stirring at room temperature, the reaction mixture was diluted with ether (300 mL) and the layers were separated. The organic layer was washed with water (3×30 mL), dried (K2CO3) and filtered. Concentration provided an oil that was purified by HPLC on silica gel (the columns were pre-treated with 10% triethylamine/hexanes, ethyl acetate and finally hexanes) eluting with a mixture of hexanes-ethyl acetate to give rac.-2- [(diphenylmethylene)amino]-3-[4-[(1,1-dimethylethoxy) carbonyl]phenyl]propanoic acid benzyl ester, (1.7 g, 3 mmol) in 36% yield.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water (3×30 mL)
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. concentrationConcentration
  6. customprovided an oil that
  7. customwas purified by HPLC on silica gel (the columns
  8. additionwere pre-treated with 10% triethylamine/hexanes, ethyl acetate and finally hexanes)
  9. washeluting with a mixture of hexanes-ethyl acetate

Sources & evidence

ORD record
ord-af75b964441d488cbe2b3864dce6506d
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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