Acetic Acid → 33605-76-4

HRID 1464210Notes

Reaction equation

HRID 1464210 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].C([O-])(=O)C.[Na+].Cl.[CH3:17][O:18][C:19](=[O:29])[C@H:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH2:21].C(O)(=O)C>C(OCC)(=O)C>[CH3:17][O:18][C:19](=[O:29])[C@H:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH:21][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%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 100.1 g of ethyl acetate, 14.3 g (0.1 mole) of N-formyl-L-aspartic anhydride was suspended, and 9.2 g (0.11 mole) of sodium acetate was added at -50°-0° C. with stirring, and 21.6 g (0.1 mole) of L-phenylalanine methyl ester hydrochloride was further added at the same temperature. 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 20.9 g (65.0% 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 99.0:1.0.

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-227af50ee4fc4616bad8f80a9e9cf9aa
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Reaction notes

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