Sodium Hydroxide → HCID 131714529, compound

HRID 1589646Notes

Reaction equation

HRID 1589646 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]([O:27]C)=[O:26])=[C:9]1[C:29]([O:31][CH2:32][CH3:33])=[O:30].[OH-].[Na+]>O1CCOCC1>[OH2:15].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]([OH:27])=[O:26])=[C:9]1[C:29]([O:31][CH2:32][CH3:33])=[O:30].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]([OH:27])=[O:26])=[C:9]1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14528708HCID 14528708, compound

Product 1

HCID 131714529HCID 131714529, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl N-(2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}ethyl)aminoacetate (2.40 g) in dioxane (80 ml) was treated with 1M aqueous sodium hydroxide solution (10 ml) and the mixture stirred at room temperature for 2 hours and then evaporated. The residue was purified by ion exchange chromatography (Bio-Rad AG 50W-X8, [Trade Mark], 200-400 mesh, cation form, 40 g) eluting with dioxane initially followed by 2% pyridine in water. Appropriate fractions were combined and evaporated to give the title compound as a hemihydrate (0.56 g), m.p. 140°-150° (decomp.).

Workup

  1. customevaporated
  2. customThe residue was purified by ion exchange chromatography (Bio-Rad AG 50W-X8, [Trade Mark], 200-400 mesh, cation form, 40 g)
  3. washeluting with dioxane
  4. customevaporated

Sources & evidence

ORD record
ord-54d841aab271412ba10788abf4f266ff
Source dataset
uspto-grants-1986_02
Patent number
US04572909

Reaction notes

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