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p-Toluenesulfonic acid → 1-{[4-(2,3-Dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methyl-3-(1,2,4-triazol-4-yl)propane

HRID 569588
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 569588
[NH2:1][CH2:2][C:3]([OH:32])([CH3:31])[CH2:4][O:5][CH2:6][C:7]1[NH:8][C:9]([CH3:30])=[C:10]([C:26]([O:28][CH3:29])=[O:27])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[Cl:25])[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].CN(C)/[CH:35]=[N:36]/[N:37]=[CH:38]/N(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:25][C:19]1[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:18]=1[CH:11]1[C:10]([C:26]([O:28][CH3:29])=[O:27])=[C:9]([CH3:30])[NH:8][C:7]([CH2:6][O:5][CH2:4][C:3]([OH:32])([CH3:31])[CH2:2][N:1]2[CH:38]=[N:37][N:36]=[CH:35]2)=[C:12]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]
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Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 9613942N'-((Dimethylamino)methylene)-N,N-dimethylformohydrazonamideHCID 148106031-Amino-3-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methylpropane

Produkt 1

HCID 148106011-{[4-(2,3-Dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methyl-3-(1,2,4-triazol-4-yl)propane
Ausbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1-amino-3-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methylpropane (0.25 g), N,N-dimethylformamide azine (0.21 g) and para-toluenesulphonic acid (10 mg) in toluene (10 ml) was heated under reflux for 1.5 hours and then partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with water, dried over Na2SO4 and evaporated. The residue was purified by chromatography on SiO2 (5 g) using dichloromethane plus 0-5% methanol as the eluant. Appropriate fractions were combined and evaporated and the residue triturated with ether. The resulting solid was collected, washed with ether and dried to give the title compound (0.18 g), m.p. 172°-176° C.

Aufarbeitung

  1. temperatureunder reflux for 1.5 hours
  2. custompartitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by chromatography on SiO2 (5 g)
  8. customevaporated
  9. customthe residue triturated with ether
  10. customThe resulting solid was collected
  11. washwashed with ether
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-aee10c1f14654c45b3f23998ceb80af7
Quelldatensatz
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04732985

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