Potassium Carbonate → N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine

HRID 345186

Reaktionsgleichung

Reaktionsgleichung von HRID 345186
[CH2:1]([NH:3][C@H:4]([C:13]([OH:15])=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[C:16]1(C)C(S(O[C@H](C)C(OCC2C=CC=CC=2)=O)(=O)=O)=CC=C[CH:21]=1.[C:39](=[O:42])([O-])[O-:40].[K+].[K+]>C(#N)C>[CH2:16]([O:14][C:13]([C@@H:4]([NH:3][C@H:1]([C:39]([OH:40])=[O:42])[CH3:2])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15])[CH3:21]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 18647272(2S)-2-(ethylamino)-4-phenylbutanoic acidHCID 86745135benzyl (R)-alpha-toluenesulfonyloxypropionate

Produkt 1

HCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ethyl (S)-homophenylalanine (I') and benzyl (R)-α-toluenesulfonyloxypropionate (II') in the presence or absence of potassium carbonate were added to acetonitrile (15 ml, bp 82° C.), and refluxed for a predetermined time, while stirring. After completing the reaction, the mixture was concentrated under reduced pressure and water (10 ml) was added to the oily residue. Then the mixture was extracted with toluene (10 ml). The organic layer was concentrated under reduced pressure to remove toluene. The oily residue was subjected to silica gel column chromatography to give the compound N-[(lS)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanine. The reaction conditions are shown in Table 3.

Aufarbeitung

  1. temperaturerefluxed for a predetermined time
  2. customthe reaction
  3. concentrationthe mixture was concentrated under reduced pressure and water (10 ml)
  4. additionwas added to the oily residue
  5. extractionThen the mixture was extracted with toluene (10 ml)
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customto remove toluene

Quellen und Nachweise

ORD-Eintrag
ord-a514b0037b054f80bd8b3b0a39c51b65
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055588

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