Acetic Anhydride → 33605-76-4

HRID 1464219Notes

Reaction equation

HRID 1464219 reaction equation
[CH:1]([NH:3][C@H:4]([C:9]([OH:11])=O)[CH2:5][C:6]([OH:8])=[O:7])=[O:2].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].Cl.[CH3:25][O:26][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH2:29]>C(O)(=O)C>[CH3:25][O:26][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:29][C:9](=[O:11])[C@H:4]([CH2:5][C:6](=[O:7])[OH:8])[NH:3][CH:1]=[O:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 88052N-formyl-L-aspartic acidHCID 517045Sodium Acetate

Product 1

HCID 1026805633605-76-4

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 28.6 g of acetic acid, 16.1 g (0.1 mole) of N-formyl L-aspartic acid was suspended and 10.2 g (0.1 mole) of acetic anhydride was added. The mixture was warmed to 50°-55° C. and stirred for 5 hours at the same temperature. After finishing the reaction, the resulting mixture was cooled to 15°-20° C. and then 9.2 g (0.11 mole) of sodium acetate and 20.5 g (0.095 mole) of L-phenylalanine methyl ester hydrochloride were successively added at the same temperature. The reaction was carried out for 4 hours with stirring at the same temperature. The reaction mixture was then concentrated and 57.2 g of water was added and cooled to 10°-15° C. Precipitated crystals were filtered, washed and dried. Crystals of N-formyl-α-L-aspartyl-L-phenylalanine methyl ester thus obtained were 28.2 g. The crystals were analyzed by high performance liquid chromatography to give a ratio of α-isomer:β-isomer of 81.0:19.0. The crystals were purified with a conventional method to give high purity crystals of N-formyl-α-L-aspartyl-L-phenylalanine methyl ester. The yield was 20.8 g (68.0% yield on L-phenylalanine methyl ester hydrochloride).

Workup

  1. temperatureThe mixture was warmed to 50°-55° C.
  2. customthe reaction
  3. temperaturethe resulting mixture was cooled to 15°-20° C.
  4. waitThe reaction was carried out for 4 hours
  5. stirringwith stirring at the same temperature
  6. concentrationThe reaction mixture was then concentrated
  7. addition57.2 g of water was added
  8. temperaturecooled to 10°-15° C
  9. customPrecipitated crystals
  10. filtrationwere filtered
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-54c844c785ef4a31896b55a803606f25
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Reaction notes

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