Methyl L-phenylalaninate hydrochloride → Rac-methyl-n-(diphenylmethylene)phenylalaninate

HRID 1841649Notes

Reaction equation

HRID 1841649 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[C:15](=N)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[N:6]=[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 136809Benzophenone imine

Product 1

HCID 11142452Rac-methyl-n-(diphenylmethylene)phenylalaninateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-phenylalanine methyl ester hydrochloride (5.95 g) and benzophenonimine (5.00 g) were added to methylene chloride (100 ml), and the mixture was stirred overnight at room temperature. The solid was filtered off from the reaction solution, and the solvent was distilled off under reduced pressure. Then, diethyl ether (100 ml) was added to the residue. The solid was filtered off again, and the ether layer was then washed with water (100 ml), and dried over anhydrous magnesium sulfate. After magnesium sulfate was removed, the ether solution was concentrated to obtain desired N-(diphenylmethylene)-L-phenylalanine methyl ester (9.44 g) in a yield of 99.6%.

Workup

  1. filtrationThe solid was filtered off from the reaction solution
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThen, diethyl ether (100 ml) was added to the residue
  4. filtrationThe solid was filtered off again
  5. washthe ether layer was then washed with water (100 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter magnesium sulfate was removed
  8. concentrationthe ether solution was concentrated

Sources & evidence

ORD record
ord-bab90e4420874a4f9f0a5a5a8fdb5658
Source dataset
uspto-grants-2004_01
Patent number
US06683214B2

Reaction notes

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