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

HRID 2290390노트

반응식

HRID 2290390 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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): ##STR71##

후처리

  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)

출처 및 근거

ORD 기록
ord-1c049dd40c994fe3be8974d5fa69cfb6
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04616038

반응 노트

불러오는 중…