Tetrahydrofuran → HCID 21201613, compound

HRID 1979422Notes

Reaction equation

HRID 1979422 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=2[N:13]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:12][CH:11]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([O:39]CC)=[O:38])[CH:32]=2)=[O:29])[C:10]1=[O:42])=[O:7].O.[OH-].[Li+].O1CCCC1>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=2[N:13]([C:21](=[O:26])[C:22]([CH3:24])([CH3:25])[CH3:23])[CH2:12][CH:11]([NH:27][C:28](=[O:29])[NH:30][C:31]2[CH:32]=[C:33]([CH:34]=[CH:35][CH:36]=2)[C:37]([OH:39])=[O:38])[C:10]1=[O:42])=[O:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21201740HCID 21201740, compound

Product 1

HCID 21201613HCID 21201613, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(Furan-2-yl)carbonylmethyl-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea (187 mg) was dissolved in methanol (8.8 ml), aqueous lithium hydroxide monohydrate (68.3 mg) solution (4.4 ml) and tetrahydrofuran (4.4 ml) were added, the mixture was refluxed for one hour. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water (50 ml), the solution was washed with diethyl ether, acidified with 1N hydrochloric acid,and extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and diisoproryl ether was added to the residue for trituration, collected by filtration, to thereby obtain 110 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 (50 ml)
  4. washthe solution was washed with diethyl ether
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure, and diisoproryl ether
  8. additionwas added to the residue for trituration
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-beb5dc4fbf074506be0d4533df796ca4
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

Loading…