Lithium hydroxide, monohydrate → 3-[3-[1-(5-methylfuran-2-yl)carbonylmethyl-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]ureido]benzoic acid

HRID 1979446Notes

Reaction equation

HRID 1979446 reaction equation
[CH3:1][C:2]1[O:6][C:5]([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](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:13][CH:12]([NH:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([O:40]CC)=[O:39])[CH:33]=3)=[O:30])[C:11]2=[O:43])=[O:8])=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO>[CH3:1][C:2]1[O:6][C:5]([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](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:13][CH:12]([NH:28][C:29](=[O:30])[NH:31][C:32]3[CH:33]=[C:34]([CH:35]=[CH:36][CH:37]=3)[C:38]([OH:40])=[O:39])[C:11]2=[O:43])=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 212018331-[1-(5-Methylfuran-2-yl)carbonylmethyl-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

Product 1

HCID 212020103-[3-[1-(5-methylfuran-2-yl)carbonylmethyl-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]ureido]benzoic acidYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[1-(5-Methylfuran-2-yl)carbonylmethyl-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea (0.80 g) was dissolved in the mixed solvent of tetrahydrofuran (10 ml) and methanol (10 ml), aqueous lithium hydroxide monohydrate (0.29 g) solution (10 ml) was added, the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, the residue was weakly acidified with 1N hydrochloric acid and extracted with chloroform. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(chloroform:methanol=20:1), to thereby obtain 442 mg of the title compound as a light yellow crystal.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography(chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-58df59686c0f494c861ade625b279564
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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