Hydrochloric Acid → 3-[4-(1-carboxy-1-(2-phenylethyl)methoxy)-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo [4,5-b]-pyridine

HRID 1492649Notes

Reaction equation

HRID 1492649 reaction equation
[C:1]([CH:6]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[O:7][C:8]1[C:13]([CH2:14][CH2:15][CH3:16])=[CH:12][C:11]([CH2:17][N:18]2[C:22]3=[N:23][C:24]([CH3:28])=[CH:25][C:26]([CH3:27])=[C:21]3[N:20]=[C:19]2[CH2:29][CH3:30])=[CH:10][C:9]=1[CH2:31][CH2:32][CH3:33])([O:3]CC)=[O:2].[OH-].[Na+].Cl>C(O)C>[C:1]([CH:6]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[O:7][C:8]1[C:13]([CH2:14][CH2:15][CH3:16])=[CH:12][C:11]([CH2:17][N:18]2[C:22]3=[N:23][C:24]([CH3:28])=[CH:25][C:26]([CH3:27])=[C:21]3[N:20]=[C:19]2[CH2:29][CH3:30])=[CH:10][C:9]=1[CH2:31][CH2:32][CH3:33])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 541604103-[4-(1-carboethoxy-1-(2-phenylethyl)methoxy)-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]-pyridine

Product 1

HCID 189505953-[4-(1-carboxy-1-(2-phenylethyl)methoxy)-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo [4,5-b]-pyridineYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred solution of 0.138 g (0.25 mmol) of the product of Step A in 1.0 mL ethanol was added 0.5 mL of a 5.0N solution of sodium hydroxide and the reaction was stirred at room temperature overnight. The reaction mixture was adjusted to pH=6 with 1.0N hydrochloric acid and then concentrated in vacuo. The residue was then purified on a silica gel flash chromatography column eluted with CHCl3 --MeOH--NH4OH (80:15:1). Evaporation of the purified fractions and drying in vacuo afforded 0.103 g (79%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was then purified on a silica gel flash chromatography column
  3. washeluted with CHCl3 --MeOH--NH4OH (80:15:1)
  4. customEvaporation of the purified fractions
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-a803a993869840f7a8197aaaa05ef209
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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