Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Methyl L-phenylalaninate hydrochloride | HCID 75736 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide | HCID 11298025 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 33605-76-4 | HCID 10268056 | 65% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05302743 |
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| Source dataset | uspto-grants-1994_04 |
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| ORD ID | ord-227af50ee4fc4616bad8f80a9e9cf9aa |
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| Source note | uspto-grants-1994_04 |
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