Acetamide → N-Acetyl-L-phenylalanine

HRID 329469

Reaktionsgleichung

Reaktionsgleichung von HRID 329469
C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:29]1([CH2:35][CH:36]=O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:38]([NH2:41])(=[O:40])[CH3:39].[C:42]([O:45]CC)(=[O:44])C>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[C:38]([NH:41][C@H:36]([C:42]([OH:45])=[O:44])[CH2:35][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)(=[O:40])[CH3:39]

Komponenten

6

Edukt 4

HCID 178AcetamideHCID 998PhenylacetaldehydeHCID 8857Ethyl AcetateHCID 742671,2-Bis(diphenylphosphino)ethane

Produkt 1

HCID 74839N-Acetyl-L-phenylalanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A glass-lined autoclave was charged with dicobalt octacarbonyl (0.68 g, 2.0 mmoles), 1,2-bis(diphenylphosphino)ethane (0.20 g), phenylacetaldehyde (6.0 g), acetamide (3.0 g) and ethyl acetate (15.0 g). The reactor was purged with CO/H2 mixture (1:1 molar ratio) to 1000 psi and with pure CO to a final pressure of 2000 psi (resulted ca. 3:1 ratio of CO to H2). The system was heated to 80° C. and held for four hours. During the process, the pressure went up to 2175 psi and then dropped to 2100 psi which indicated the gas consumption. After the reactor was cooled to room temperature, a deep-brown homogeneous solution (ca. 25.9 g) was recovered. A portion of product solution was subjected to a high-vacuum to remove solvent and then analyzed. N-acetylphenylalanine was obtained at ca. 72 mole % yield based on phenylacetaldehyde charged. The cobalt analysis showed 9950 ppm cobalt in product solution; estimated cobalt recovery in solution was >98%:

Aufarbeitung

  1. customThe reactor was purged with CO/H2 mixture (1:1 molar ratio) to 1000 psi and with pure CO to a final
  2. custompressure of 2000 psi (resulted ca. 3:1 ratio of CO to H2)
  3. additiondropped to 2100 psi which
  4. customthe gas consumption
  5. temperatureAfter the reactor was cooled to room temperature
  6. customa deep-brown homogeneous solution (ca. 25.9 g) was recovered
  7. customto remove solvent

Quellen und Nachweise

ORD-Eintrag
ord-030ddd5bba7d413ebbd51fed1cc14579
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891442

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