Cinchonidine → (R)-1-(2-methoxyethoxy)methyl-2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine

HRID 34402

Reaktionsgleichung

Reaktionsgleichung von HRID 34402
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=[O:15])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:9]([C:26]([O:28][CH3:29])=[O:27])=[C:8]1[CH3:30].C=C[C@@H]1[C@@H]2C[C@@H]([C@H](O)C3C=CN=C4C=CC=CC=34)N(CC2)C1>CCO>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=[O:15])[C@@H:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:9]([C:26]([O:28][CH3:29])=[O:27])=[C:8]1[CH3:30]

Komponenten

4

Edukt 2

HCID 101744CinchonidineHCID 14208794(+)-1-(2-Methoxyethoxymethyl)-2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine

Produkt 1

HCID 14208796(R)-1-(2-methoxyethoxy)methyl-2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The racemic N-protected mono-ester of formula 18 is then dissolved in a suitable lower alkanol solvent at about the solvent reflux temperature along with a suitable optically active base, and the resulting salt allowed to crystallize as the solution cools to provide the optically resolved salt of either the (R)-18 or (S)-18. (It is preferred to recrystallize the resulting optically active salt to obtain a higher degree of purity.) For example, (RS)-1-(2-methoxyethoxy)methyl-2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine is dissolved in EtOH at reflux temperature along with one molar equivalent of cinchonidine, and the mixture allowed to stand at room temperature overnight. The resulting crystals are recrystallized twice from EtOH to yield the pure (R)-18 salt, (R)-1-(2-methoxyethoxy)methyl-2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine.cinchonidine. (Scheme VI, Step 3)

Aufarbeitung

  1. temperaturereflux temperature along with a suitable optically active base
  2. customto crystallize as the solution
  3. customto provide the optically resolved salt of either the (R)-18 or (S)-18
  4. customto recrystallize the resulting optically active salt
  5. customto obtain a higher degree of purity
  6. customThe resulting crystals are recrystallized twice from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-d6ac2fb5ba9449b696c383cb13dd32fa
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761420

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