Lithium hydroxide, monohydrate → HCID 21201560, compound

HRID 1979353Notes

Reaction equation

HRID 1979353 reaction equation
[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=2[N:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:11][CH:10]([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:9]1=[O:42])=[O:6])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.C(O)C>[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=2[N:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:11][CH:10]([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:9]1=[O:42])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21201591HCID 21201591, compound

Product 1

HCID 21201560HCID 21201560, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(1-tert-Butylcarbonylmethyl-2-oxo-5-phenyl-8-methoxy-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-ethoxycarbonylphenyl)urea (1.17 g) was dissolved in a mixed solvent of tetrahydrofuran (20 ml) and ethanol (20 ml), aqueous lithium hydroxide monohydrate (428 mg) solution (10 ml) was added, and the mixture was stirred for 7 hours at room temperature. The reaction mixture was concentrated under reduced pressure, the residue was weakly acidified with 1N hydrochloric acid, extracted with chloroform. The organic layer was successively washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was suspended in ethyl acetate for trituration, collected by filtration, to thereby obtain 616 mg of the titled compound.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with chloroform
  4. washThe organic layer was successively washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5dc0dcaa7ac848ef82727e74a3f654bd
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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