Lithium hydroxide, monohydrate → HCID 21201824, compound

HRID 1979303Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

1-(tert-butylcarbonylmethyl-2-oxo-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-ethoxycarbonylphenyl)urea (500 mg) was dissolved in methanol (20 ml), the solution of lithium hydroxide monohydrate (191 mg) in water (10 ml) was added, the mixture was stirred at 50° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, after acidification with 1N hydrochloric acid, the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and recrystallized from ethanol and isopropyl ether, to thereby obtain 380 mg of the titled compound (Yield: 73%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionafter acidification with 1N hydrochloric acid, the mixture was extracted with chloroform
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customrecrystallized from ethanol and isopropyl ether

Sources & evidence

ORD record: ord-6fd3fe2660344b25b7c54807e69b819d
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239131B1

Reaction notes

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