18-Crown-6 → 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-1-yl)propane

HRID 329684

反応式

HRID 329684 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]2([CH3:26])[CH2:25][O:24]2)=[C:10]1[C:27]([O:29][CH2:30][CH3:31])=[O:28].[Na].[NH:33]1[CH:37]=[N:36][CH:35]=[N:34]1.C1OCCOCCOCCOCCOCCOC1>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]([OH:24])([CH3:26])[CH2:25][N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)=[C:10]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

参加物

5

反応物 3

HCID 2855718-Crown-6HCID 148105962-{[4-(2,3-Dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxymethyl}-2-methyloxiraneHCID 454898221h-1,2,4-Triazole sodium salt

生成物 1

HCID 201476751-{[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-1-yl)propane収率 53.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxymethyl}-2-methyloxirane (0.80 g), 1,2,4-triazole sodium salt (0.60 g) and "18-Crown-6" (20 mg) in tetrahydrofuran (25 ml) was stirred at room temperature for two days 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 (12 g) using toluene plus 0-100% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated and the residue was triturated with ether. The resulting solid was collected, washed with ether and dried to give the title compound (0.49 g), m.p. 149°-160° C.

後処理

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

出典と根拠

ORDレコード
ord-443e1c0bd65a4e88a3a84096de3ab4e7
出典データセット
uspto-grants-1990_01
特許番号
US04892881

関連ノート

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