Benzophenone imine → HCID 11119053, compound

HRID 1944561Notes

Reaction equation

HRID 1944561 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].[C:9](=N)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.O>[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[N:6]=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 136809Benzophenone imineHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 11119053HCID 11119053, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of alanine methyl ester hydrochloride (10.0 g, 71.6 mmol) in 100 mL CH2Cl2 was added benzophenone imine (12.0 mL, 71.6 mmol). A white ppt gradually came out of solution as the reaction was allowed to proceed at rt for 15 h. The reaction was diluted with H2O and CH2Cl2, and the layers were separate, the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to afford methyl-N-(diphenylmethylene)alaninate as a viscous oil which was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 7.62 (m, 2H), 7.47-7.29 (m, 6H), 7.19-7.16 (m, 2H), 4.16 (q, J =6.8 Hz, 1H), 3.7 (s, 3H, 1.40 (d, J=6.8 Hz, 3H).

Workup

  1. customthe layers were separate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe469f0d197e4a118b517b651c865a73
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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