Acetic Acid → 33605-76-4

HRID 1464213Notes

Reaction equation

HRID 1464213 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:9](=[O:10])[O:8][C:6](=[O:7])[CH2:5]1)=[O:2].Cl.[CH3:12][O:13][C:14](=[O:24])[C@H:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:16].C([O-])(=O)C.[Na+].C(O)(=O)C>C(OCC)(=O)C>[CH3:12][O:13][C:14](=[O:24])[C@H:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:16][C:9](=[O:10])[C@H:4]([CH2:5][C:6](=[O:7])[OH:8])[NH:3][CH:1]=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 517045Sodium AcetateHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Product 1

HCID 1026805633605-76-4Yield 65.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 100 g of ethyl acetate, 14.3 g (0.1 mole) of N-formyl-L-aspartic anhydride and 21.6 g (0.1 mole) of L-phenylalanine methyl ester hydrochloride were suspended and 9.2 g (0.11 mole) of sodium acetate was added to the suspension during 30 minutes at 20°-25° C. with stirring. The mixture was reacted for 5 hours with stirring at the same temperature. Thereafter 14.3 g of acetic acid was added and stirred for an hour at the same temperature. Precipitated crystals were filtered, washed and dried. Crystals of N-formyl-α-L-aspartyl-L-phenylalanine methyl ester were obtained in a yield of 21.1 g (65.5% yield on L-Phenylalanine methyl ester hydrochloride). The crystals obtained were analyzed by high performance liquid chromatography to give a ratio of α-isomer:β-isomer of 98.0:2.0.

Workup

  1. customThe mixture was reacted for 5 hours
  2. stirringwith stirring at the same temperature
  3. stirringstirred for an hour at the same temperature
  4. customPrecipitated crystals
  5. filtrationwere filtered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-e62dd2805f2c47778a8b85cf2d6d9202
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Reaction notes

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