Tetrahydrofuran → HCID 21201685, compound

HRID 1979391Notes

Reaction equation

HRID 1979391 reaction equation
[C:1]1([CH3:46])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[O:23])[CH2:13][CH:12]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([O:42]CC)=[O:41])[CH:35]=3)=[O:32])[C:11]2=[O:45])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.O.[OH-].[Li+].O1CCCC1>CO>[C:1]1([CH3:46])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[O:23])[CH2:13][CH:12]([NH:30][C:31](=[O:32])[NH:33][C:34]3[CH:35]=[C:36]([CH:37]=[CH:38][CH:39]=3)[C:40]([OH:42])=[O:41])[C:11]2=[O:45])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 697003921-[1-(2-toluoylmethy)-2-oxo-5-(2-pyridylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

Product 1

HCID 21201685HCID 21201685, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(2-Toluoylmethy)-2-oxo-5-(2-pyridylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea (466 mg) was dissolved in methanol (22 ml), aqueous lithium hydroxide monohydrate (158 mg) solution (11 mg) and tetrahydrofuran (11 ml) were added, and the mixture was refluxed for one hour. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water, the solution was washed with diethyl ether, acidified with 1N hydrochloric acid, and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Isopropyl ether was added to the residue for trituration, collected by filtration, to thereby obtain 203 mg of the titled compound.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washthe solution was washed with diethyl ether
  5. extractionextracted with methylene chloride
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. additionIsopropyl ether was added to the residue for trituration
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9233b9f48e4d4212a51aedc569fc805d
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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