Benzene → N-acetyl-(R)-phenyl-alanine

HRID 223789

Reaktionsgleichung

Reaktionsgleichung von HRID 223789
[C:1]([NH:4][C:5](=[CH:9]C1C=CC=CC=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H][H]>F[B-](F)(F)F.[Rh+3].C1(P(C2C=CC=CC=2)C[C@@H](P(C2C=CC=CC=2)C2C=CC=CC=2)CC2C=CC=CC=2)C=CC=CC=1.C1CCCCC=CC=1.F[B-](F)(F)F.F[B-](F)(F)F.CCO>[C:1]([N:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:5]([C:6]([OH:8])=[O:7])[CH3:9])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 241BenzeneHCID 956312-(Acetylamino)-3-phenyl-2-propenoic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 821174N-acetyl-(R)-phenyl-alanineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 86738616cyclo-octadiene-((S)-1,2-Bis-(diphenylphosphino)-3-phenyl-propane)-rhodium-tetrafluoroborateKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

There were added saturated solution of α-acetamido cinnamic acid in a mixture of 2 parts by volume of ethanol and 1 part by volume of benzene 7.9 mg of the catalyst produced in Example 12. The reaction mixture was sucked into an evacuated 100 ml autoclave and pressurized with 17 bars of hydrogen pressure. After working up in the manner as described in Example 6, there were isolated 4.4 grams of N-acetyl-(R)-phenyl-alanine having a rotary value of [α]D20 =-46.5° (c=1/95% EtOH), corresponding to an optical yield of 99%.

Quellen und Nachweise

ORD-Eintrag
ord-008c63fd9da74710bae5d9f2cc8ef5fc
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04356324

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