2-((4-((2-(1-Methylethoxy)ethoxy)methyl)phenoxy)methyl)oxirane → 1,4-Dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{{{2-{{p-{2-[[3-[4-(2-isopropoxyethoxymethyl)-phenoxy]-2-hydroxypropylamino]]-2-methylpropoxy}-phenoxy}}-ethyl}}}-ester 5-methyl ester

HRID 620088Notes

Reaction equation

HRID 620088 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[CH:32]=2)[C:7]([C:13]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([NH2:30])([CH3:29])[CH3:28])=[CH:21][CH:20]=2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4].[O:40]1[CH2:58][CH:41]1[CH2:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][O:51][CH2:52][CH2:53][O:54][CH:55]([CH3:57])[CH3:56])=[CH:46][CH:45]=1>C(O)(C)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[CH:32]=2)[C:7]([C:13]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([NH:30][CH2:58][CH:41]([OH:40])[CH2:42][O:43][C:44]3[CH:49]=[CH:48][C:47]([CH2:50][O:51][CH2:52][CH2:53][O:54][CH:55]([CH3:57])[CH3:56])=[CH:46][CH:45]=3)([CH3:29])[CH3:28])=[CH:21][CH:20]=2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4]

Participants

4

Reactant 2

HCID 151078092-((4-((2-(1-Methylethoxy)ethoxy)methyl)phenoxy)methyl)oxiraneHCID 703937091,4-Dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{2-[p-(2-amino-2-methylpropoxy)-phenoxy]-ethyl}-ester 5-methyl ester

Product 1

HCID 703938061,4-Dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{{{2-{{p-{2-[[3-[4-(2-isopropoxyethoxymethyl)-phenoxy]-2-hydroxypropylamino]]-2-methylpropoxy}-phenoxy}}-ethyl}}}-ester 5-methyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4.6 g (8.5 mmol) of 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{2-[p-(2-amino-2-methylpropoxy)-phenoxy]-ethyl}-ester 5-methyl ester and 2.95 g (11 mmol) of 1-(2,3-epoxypropoxy)-4-[2-(isopropoxy)-ethoxymethyl]-benzene in 20 ml of isopropanol is heated under reflux for 6 hours while stirring. Working up and chromatographic purification analogously to Example 1 yield 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{{{2-{{p-{2-[[3-[4-(2-isopropoxyethoxymethyl)-phenoxy]-2-hydroxypropylamino]]-2-methylpropoxy}-phenoxy}}-ethyl}}}-ester 5-methyl ester in the form of a vitreous solid having the structure: ##STR38##

Workup

  1. temperatureunder reflux for 6 hours
  2. customWorking up and chromatographic purification analogously to Example 1

Sources & evidence

ORD record
ord-8b053799ca474cf4ad134e2f7c29068d
Source dataset
uspto-grants-1989_04
Patent number
US04818766

Reaction notes

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