Phosphorus trichloride → N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

HRID 325270

Reaktionsgleichung

Reaktionsgleichung von HRID 325270
[C:1]([NH:7][C@H:8]([C:13]([O-:15])=O)[CH2:9][C:10]([O-:12])=[O:11])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Na+].[Na+].P(Cl)(Cl)Cl.C(N[C@@H]1C(=O)OC(=O)C1)(=O)CC(C)=O.[CH3:36][O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH2:40]>O1CCOCC1.C(O)(=O)C.C(OCC)(=O)C>[CH3:36][O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:40][C:13](=[O:15])[C@H:8]([CH2:9][C:10](=[O:11])[OH:12])[NH:7][C:1](=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Komponenten

8

Edukt 4

HCID 24387Phosphorus trichlorideHCID 736234L-Phenylalanine, methyl esterHCID 13334674N-acetoacetyl-L-aspartic anhydrideHCID 86739332Disodium N-acetoacetylaspartate

Produkt 1

HCID 13334676N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Crude disodium N-acetoacetylaspartate, 28.51 parts, was stirred with 200 parts by volume of ethyl acetate and 11.7 parts by volume of acetic acid at 0°-5° C. under argon while 4.37 parts by volume of phosphorous trichloride was added dropwise. The resulting mixture was allowed to warm to ambient temperatures while stirring for 20 hours. To the resulting solution which contains N-acetoacetyl-L-aspartic anhydride was added dropwise over a 2 hour period 122 parts by volume of 0.9 M L-phenylalanine methyl ester in dioxane. After continued stirring for 20 hours, the solvent was evaporated under vacuum at 35°-40° C. Toluene, 200 parts by volume, was added to the residue and the evaporation was repeated, giving crude N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester as a semi-solid yellow residue.

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureto warm to ambient temperatures
  3. stirringAfter continued stirring for 20 hours
  4. customthe solvent was evaporated under vacuum at 35°-40° C
  5. additionToluene, 200 parts by volume, was added to the residue
  6. customthe evaporation

Quellen und Nachweise

ORD-Eintrag
ord-ae02da52df18469f80af1069646dabb4
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04440677

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