Hydrochloric Acid → 2-butyl-3-[4-[(1-carboxy)(1-phenyl)methoxy]-3-chlorophenyl]methyl-6-methylquinazolin-4(3H)-one

HRID 257826Notes

Reaction equation

HRID 257826 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([C:30]([O:32]C)=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:18]([Cl:34])[CH:17]=2)[C:13](=[O:35])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:36])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([C:30]([OH:32])=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:18]([Cl:34])[CH:17]=2)[C:13](=[O:35])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:36])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 199348532-butyl-3-[4-[(1-carbomethoxy) (1-phenyl)methoxy]-3-chlorophenyl]methyl-6-methylquinazolin-4(3H)-one

Product 1

HCID 152893922-butyl-3-[4-[(1-carboxy)(1-phenyl)methoxy]-3-chlorophenyl]methyl-6-methylquinazolin-4(3H)-oneYield 71.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 72 mg of the product of Step C dissolved in 2 mL of methanol, was added 0.25 mL of a 1N solution of NaOH and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was then adjusted to pH 7 with 1N HCl, caoncentrated in vacuo, and the residue was applied to a silica gel flash chromatography column and eluted with CHCl3 /MeOH/NH4OH (80:15:1). Evaporation of the purified fractions and drying in vacuo afforded 50 mg (71%) of the title compound.

Workup

  1. washeluted with CHCl3 /MeOH/NH4OH (80:15:1)
  2. customEvaporation of the purified fractions
  3. customdrying in vacuo

Sources & evidence

ORD record
ord-1f9b4332afbc4ae799f922c2b0715173
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

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