Lithium hydroxide, monohydrate → HCID 21201792, compound

HRID 1979480Notes

Reaction equation

HRID 1979480 reaction equation
O.[OH-].[Li+].[C:4]([C:8]([CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:14][CH:13]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[C:36]([C:38]([O:40]C)=[O:39])[CH:35]=[C:34]([C:42]([O:44]C)=[O:43])[CH:33]=2)=[O:30])[C:12]1=[O:46])=[O:9])([CH3:7])([CH3:6])[CH3:5]>O1CCCC1>[C:4]([C:8]([CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:14][CH:13]([NH:28][C:29](=[O:30])[NH:31][C:32]2[CH:33]=[C:34]([C:42]([OH:44])=[O:43])[CH:35]=[C:36]([CH:37]=2)[C:38]([OH:40])=[O:39])[C:12]1=[O:46])=[O:9])([CH3:7])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21201942HCID 21201942, compound

Product 1

HCID 21201792HCID 21201792, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Aqueous lithium hydroxide monohydrate (420 mg) solution (20 ml) was added to a solution of 1-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-[3,5-bis(methoxycarbonyl)phenyl]urea (593 mg) in tetrahydrofuran (20 ml), the mixture was stirred at 50° C. for 2 hours. After allowed to cool, the reaction mixture was concentrated under reduced pressure, the residue was acidified with 1N hydrochloric acid, extracted with the mixed solvent of chloroform and methanol (5:1), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, Isopropyl alcohol was added to the residue, crystals so precipitated were collected by filtration, to thereby obtain 420 mg of the title compound (Yield: 74%).

Workup

  1. temperatureto cool
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with the mixed solvent of chloroform and methanol (5:1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure, Isopropyl alcohol
  6. additionwas added to the residue, crystals
  7. customso precipitated
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7ae0214dbbbf4941a7a13584752205b4
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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