Hydrochloric Acid → HCID 57425272, compound

HRID 989455Notes

Reaction equation

HRID 989455 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:14](=N)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[C:15]1([C:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 136809Benzophenone imine

Product 1

HCID 57425272HCID 57425272, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrochloride of methyl ester of L-phenylalanine (5.95 g) and benzophenoneimine (5.00 g) were added to methylene chloride (100 ml), and they were stirred at room temperature overnight. A solid thus formed was filtered out of the reaction mixture. The filtrate was concentrated under reduced pressure. Diethyl ether (100 ml) was added to the residue. A solid thus formed was again filtered out of the reaction mixture. The ether layer was washed with water (100 ml) and then dried over anhydrous magnesium sulfate. Magnesium sulfate was removed, and the solution in ether was concentrated to obtain the intended methyl ester of N-(diphenylmethylene)-L-phenylalanine (9.44 g) in a yield of 99.6%.

Workup

  1. customA solid thus formed
  2. filtrationwas filtered out of the reaction mixture
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionDiethyl ether (100 ml) was added to the residue
  5. customA solid thus formed
  6. filtrationwas again filtered out of the reaction mixture
  7. washThe ether layer was washed with water (100 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customMagnesium sulfate was removed
  10. concentrationthe solution in ether was concentrated

Sources & evidence

ORD record
ord-c5ea50cb82b24c4bb8d48430be363d5d
Source dataset
uspto-grants-2003_10
Patent number
US06639094B2

Reaction notes

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