Triethylamine → 10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)-decanoyl-D-phenylalanine

HRID 1382676

Reaktionsgleichung

Reaktionsgleichung von HRID 1382676
[CH3:1][O:2][C:3]1[C:4](=[O:34])[C:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]C2C=CC([N+]([O-])=O)=CC=2)=O)=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].[NH2:35][C@@H:36]([C:44]([OH:46])=[O:45])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4](=[O:34])[C:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH:35][C@@H:36]([C:44]([OH:46])=[O:45])[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:24])=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 71567D-PhenylalanineHCID 12818692p-Nitrophenyl 10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoate

Produkt 1

HCID 1351852410-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)-decanoyl-D-phenylalanineAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of p-nitrophenyl 10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoate (4.73 g, 10 mmol) and D-phenylalanine (1.65 g, 10 mmol) in N,N-dimethylformamide (30 ml), was added triethylamine (1.4 ml, 10 mmol). The mixture was stirred at room temperature for 2 days, whereupon the insoluble matter almost disappeared. The solvent was distilled off under reduced pressure and the residue was chromatographed on a column of silica gel (100 g). The column was washed well with chloroform and elution with chloroform-methanol-acetic acid (18:2:1, v/v) gave 10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoyl-D-phenylalanine (2.56 g), melting at 96°-98° C., after washing up in the usual way.

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was chromatographed on a column of silica gel (100 g)
  3. washThe column was washed well with chloroform and elution with chloroform-methanol-acetic acid (18:2:1

Quellen und Nachweise

ORD-Eintrag
ord-bdbe823f2690429b841b4baca8e741ba
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808339

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