Hydrochloric Acid → HCID 21201864, compound

HRID 1979454Notes

Reaction equation

HRID 1979454 reaction equation
[N:1]1([C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:12][CH:11]([NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][C:33](C(OCC)=O)=[CH:32][CH:31]=3)=[O:28])[C:10]2=[O:41])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:42].[Li+].[CH3:44][OH:45].Cl>O1CCCC1.C(Cl)(Cl)Cl>[N:1]1([C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:12][CH:11]([NH:26][C:27](=[O:28])[NH:29][C:30]3[CH:31]=[C:32]([CH:33]=[CH:34][CH:35]=3)[C:44]([OH:45])=[O:42])[C:10]2=[O:41])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 21201721HCID 21201721, compound

Product 1

HCID 21201864HCID 21201864, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

1-[1-(Pyrrolidin-1-ylcarbonylmethyl)-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(4-ethoxycarbonylphenyl)urea was suspended in tetrahydrofuran (20 ml), aqueous lithium hydroxide (0.37 g) solution (10 ml) and methanol (20 ml) were added, the mixture was stirred at 40-50° C. for one hour. 1N hydrochloric acid and chloroform were added and extracted. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, isopropyl ether was added to crystals so precipitated for trituration, collected by filtration, to thereby obtain 0.81 g of the title compound (Yield: 85.1%).

Workup

  1. extractionextracted
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure, isopropyl ether
  5. additionwas added to crystals
  6. customso precipitated for trituration
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f917d4a95af8496198aefc1872a76005
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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