Boc-N-Me-Phe-OH → N-Boc-N-methyl-3-cyclohexanyl-L-alanine

HRID 746231

Reaktionsgleichung

Reaktionsgleichung von HRID 746231
[C:1]([O:5][C:6]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>O1CCCC1.[Rh]>[C:1]([O:5][C:6]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

5

Edukt 2

HCID 7010602Boc-N-Me-Phe-OHHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 66590605N-Boc-N-methyl-3-cyclohexanyl-L-alanineAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23948RhodiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4.8 g of t-butoxycarbonyl-N-methylphenylalanine in 150 ml of tetrahydrofuran was hydrogenated at 60° for about four days using 60 psi hydrogen gas and 5% rhodium on carbon. The mixture was filtered and the filtrate concentrated to give the title compound (3.5 g) as a colorless oil. The oil was used without further purification. Structure assignment was supported by the nmr spectrum (loss of aromatic protons and appearance of cyclohexyl protons) and by elemental analysis.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3dcd5c79227146e9b2fa48517e5cdbab
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04603121

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