2-Oxooctanoic acid → Z-2-(2,2-dichlorocyclopropanecarboxamido)-2-octenoic acid

HRID 1885848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885848
O=[C:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4].[Cl:12][C:13]1([Cl:19])[CH2:15][CH:14]1[C:16]([NH2:18])=[O:17]>C1(C)C=CC=CC=1>[Cl:12][C:13]1([Cl:19])[CH2:15][CH:14]1[C:16]([NH:18]/[C:2](=[CH:6]\[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])/[C:3]([OH:5])=[O:4])=[O:17]

Komponenten

4

Edukt 2

HCID 676002-Oxooctanoic acidHCID 5419272,2-Dichlorocyclopropane-1-carboxamide

Produkt 1

HCID 44267683Z-2-(2,2-dichlorocyclopropanecarboxamido)-2-octenoic acidAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1.19 g (7.5 mmoles) of 2-ketooctanoic acid, 0.77 g (5.0 mmoles) of 2,2-dichlorocyclopropanecarboxamide, and 5 ml toluene were reacted using the same procedure as in the previous example. The crude product (537 mg) was purified by conversion to the methyl ester (BF3 /CH3OH), preparative TLC (silica gel G, 4:1 hexane-EtOAc) and saponification of the pure Z-methyl ester (0.3M LiOH/CH3OH) to give 88 mg of Z-2-(2,2-dichlorocyclopropanecarboxamido)-2-octenoic acid as a partially crystalline gum. NMR spectrum (DMSO-d6): δ9.68 (s, 1H, NH), 6.50 δ (t, 1H, ##STR72## 2.83δ (t, 1H, ##STR73## 1.97 δ (d, 2H ##STR74## 0.87 δ (t, 3H, CH3).

Aufarbeitung

  1. customwere reacted
  2. customThe crude product (537 mg) was purified by conversion to the methyl ester (BF3 /CH3OH), preparative TLC (silica gel G, 4:1 hexane-EtOAc) and saponification of the pure Z-methyl ester (0.3M LiOH/CH3OH)

Quellen und Nachweise

ORD-Eintrag
ord-bca91c5f9a0142499c4ad5fe99158075
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05147868

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