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

HRID 1460435Notes

Reaction equation

HRID 1460435 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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), prepartive 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): 9.68δ (s, 1H, NH), 6.50δ (t, 1H, ##STR74## 2.83δ (t, 1H, 1.97δ (d, ##STR75## 0.87δ (t, 3H, CH3).

Workup

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

Sources & evidence

ORD record
ord-032f324745ca4783b7515a69a950b938
Source dataset
uspto-grants-1991_12
Patent number
US05071843

Reaction notes

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