Hydrochloric Acid → 5-Carboxy-2-methylthiomethyl-6-methyl-4-(3-nitrophenyl)-3-carboethoxy-1,4-dihydropyridine

HRID 5652

Reaktionsgleichung

Reaktionsgleichung von HRID 5652
[CH3:1][S:2][CH2:3][C:4]1[NH:5][C:6]([CH3:30])=[C:7]([C:24]([O:26]CC=C)=[O:25])[CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].C([O-])=O.[NH4+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>[Pd].O1CCOCC1>[C:24]([C:7]1[CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH2:3][S:2][CH3:1])[NH:5][C:6]=1[CH3:30])([OH:26])=[O:25]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 2723923Ammonium formateHCID 197964192-Methylthiomethyl-6-methyl-4-(3-nitrophenyl)-3-carboethoxy-5-carboallyloxy-1,4-dihydropyridine

Produkt 1

HCID 197965185-Carboxy-2-methylthiomethyl-6-methyl-4-(3-nitrophenyl)-3-carboethoxy-1,4-dihydropyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of 2-methylthiomethyl-6-methyl-4-(3-nitrophenyl)-3-carboethoxy-5-carboallyloxy-1,4-dihydropyridine (g 0.27), palladium on charcoal (10% 6 mg), ammonium formate (mg 71) and triphenylphosphine (mg 3) in anhydrous 1,4-dioxane, is heated at the reflux temperature for 8 hours. The reaction mixture is cooled at room temperature, poured into an aqueous solution of hydrochloric acid (pH=2) and extracted with ethyl acetate (2×20 ml). The combined organic extracts are washed with aqueous sodium carbonate (1N; 3×10 l), the basic washings are collected, acidified to pH 5-6 with diluted aqueous hydrochloric acid. The resulting suspension is extracted with ethyl acetate (2×25 ml) the combined organic extracts are dried on Na2SO4 and evaporated under reduced pressure to give mg 160 of 5-carboxy-2-methylthiomethyl-6-methyl-4-(3-nitrophenyl)-3-carboethoxy-1,4-dihydropyridine as an amorphous solid.

Aufarbeitung

  1. temperatureis heated at the reflux temperature for 8 hours
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. washThe combined organic extracts are washed with aqueous sodium carbonate (1N; 3×10 l)
  4. customthe basic washings are collected
  5. extractionThe resulting suspension is extracted with ethyl acetate (2×25 ml) the combined organic extracts
  6. customare dried on Na2SO4
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6c49a90aeb7b4f16adbda904ec4ca422
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245039

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