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

Reaction equation

HRID 329684 reaction equation
[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]

Participants

5

Reactant 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

Product 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)propaneYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-443e1c0bd65a4e88a3a84096de3ab4e7
Source dataset
uspto-grants-1990_01
Patent number
US04892881

Linked notes

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