Potassium Carbonate → N-(Diphenylmethylene)glycine tert-butyl ester

HRID 1242853Notes

Reaction equation

HRID 1242853 reaction equation
Cl[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10](=[NH:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:6]([O:5][C:3](=[O:4])[CH2:2][N:23]=[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 136809Benzophenone imine

Product 1

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

In a 50-mL round-bottom flask equipped with a water-jacketed condensor and magnetic stirring bar, a mixture of t-butyl chloroacetate (10 g, 66.4 mmole), benzophenone imine (8.02 g, 44.3 mmole), and anhydrous potassium carbonate (9.18 g, 66.4 mmole) was stirred overnight at 110° C. Using a course Buchner funnel, the solid inorganic salts were removed from the solution by filtration and the solids were washed with ethyl acetate (2×25 mL). The combined filtrates were diluted with ethyl acetate to a total volume of 100 mL. The organic mixture was washed with water (3×100 mL), dried (Na2SO4), filtered, and the solvent was removed in vacuo. The crude residue was recrystallized with hexanes to afford white crystals (5.24 g, 40%): m.p. 114–115° C. (Lit. m.p. 111–112° C.).3 1H-NMR (CDCl3) δ 1.46 (s, 9H), 4.12 (s, 2H), 7.18 (m, 2H), 7.34 (m, 3H), 7.45 (m, 3H), 7.66 (m, 2H). 13C-NMR (CDCl3) δ 28.13, 56.37, 80.99, 127.74, 128.01, 128.27, 128.61, 128.73, 128.76, 130.05, 130.34, 132.39, 136.25, 139.45, 169.82, 171.48

Workup

  1. customthe solid inorganic salts were removed from the solution by filtration
  2. washthe solids were washed with ethyl acetate (2×25 mL)
  3. additionThe combined filtrates were diluted with ethyl acetate to a total volume of 100 mL
  4. washThe organic mixture was washed with water (3×100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe crude residue was recrystallized with hexanes

Sources & evidence

ORD record
ord-8a3a5f94abb84640a1843b3220a9b99e
Source dataset
uspto-grants-2006_10
Patent number
US07115766B2

Reaction notes

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