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

HRID 34402

反応式

HRID 34402 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-d6ac2fb5ba9449b696c383cb13dd32fa
出典データセット
uspto-grants-1988_08
特許番号
US04761420

関連ノート

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