Sodium Hydroxide → Zenarestat

HRID 1639311Notes

Reaction equation

HRID 1639311 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][C:12]([Cl:18])=[CH:13][CH:14]=3)[N:9]([CH2:19][C:20]([O:22]CC)=[O:21])[C:8]2=[O:25])=[C:4]([F:28])[CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][C:12]([Cl:18])=[CH:13][CH:14]=3)[N:9]([CH2:19][C:20]([OH:22])=[O:21])[C:8]2=[O:25])=[C:4]([F:28])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11431340Ethyl {3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}acetate

Product 1

HCID 5724ZenarestatYield 84.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-[3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate (249 g) and 1N aqueous sodium hydroxide (795 ml) in methanol (1.6 l) was refluxed for 30 minutes with stirring. The solvent was evaporated and the residue was dissolved in hot water (5 l). The aqueous solution was poured into ice-cold 0.5N hydrochloric acid (3 l). The precipitates were collected by filtration and recrystallized from a mixture of ethanol (6 l) and water (3 l) to give 2-[3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetic acid (198 g).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in hot water (5 l)
  4. additionThe aqueous solution was poured into ice-cold 0.5N hydrochloric acid (3 l)
  5. filtrationThe precipitates were collected by filtration
  6. customrecrystallized from a mixture of ethanol (6 l) and water (3 l)

Sources & evidence

ORD record
ord-f54c49f57f7a489cbdcee0957654de95
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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