Phenyl glycidyl ether → Dimethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4665

Reaction equation

HRID 4665 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][C:8]=1[CH:17]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([CH3:27])[NH:20][C:19]([CH3:28])=[C:18]1[C:29]([O:31][CH3:32])=[O:30].[C:33]1([O:39][CH2:40][CH:41]2[O:43][CH2:42]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CO>[OH:43][CH:41]([CH2:40][O:39][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:42][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:14])=[O:15])=[CH:9][C:8]=1[CH:17]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([CH3:27])[NH:20][C:19]([CH3:28])=[C:18]1[C:29]([O:31][CH3:32])=[O:30]

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 14050493Dimethyl 4-[2-(4-aminobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 14050450Dimethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 30.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 44 ml of methanol were dissolved 2.57 g of dimethyl 4-[2-(4-aminobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (obtained in Reference Example 2) and 0.83 g of glycidyl phenyl ether, and the solution formed was allowed to react at room temperature for 43 hours and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chloroform-methanol (95:5 v/v). Crude crystals were recrystallized from ethanol-ether to give 1.05 g of dimethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. customthe solution formed
  2. customto react at room temperature for 43 hours
  3. concentrationconcentrated under reduced pressure
  4. washthe product was eluted with chloroform-methanol (95:5 v/v)
  5. customCrude crystals were recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-95616be347ab446d930fbf2dcab17c14
Source dataset
uspto-grants-1988_02
Patent number
US04727082

Linked notes

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