Lithium hydroxide, monohydrate → [(Z)-1-[4-(2-Biphenylylcarbonylamino)benzoyl]-4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepine-5-ylidene]acetic acid

HRID 726708Notes

Reaction equation

HRID 726708 reaction equation
[F:1][C:2]1([F:41])[CH2:3][CH2:4][N:5]([C:18](=[O:40])[C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:39])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:21][CH:20]=2)[C:6]2[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=2/[C:8]/1=[CH:9]/[C:10]([O:12]C)=[O:11].O.[OH-].[Li+]>CO>[F:41][C:2]1([F:1])[CH2:3][CH2:4][N:5]([C:18](=[O:40])[C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:39])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[CH:21][CH:20]=2)[C:6]2[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=2/[C:8]/1=[CH:9]/[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10602784[(Z)-1-[4-(2-Biphenylylcarbonylamino)benzoyl]-4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepine-5-ylidene]acetic acid methyl ester

Product 1

HCID 10554393[(Z)-1-[4-(2-Biphenylylcarbonylamino)benzoyl]-4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepine-5-ylidene]acetic acidYield 75.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (Z)-[4,4-difluoro-1-[4-(2phenylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetate (857 mg) was dissolved in 10 ml of methanol, 2 ml of aqueous solution containing 195 mg of lithium hydroxide monohydrate was added dropwise to the above solution under ice-cooling, and the mixture was stirred at room temperature for 7 hours. After evaporating the solvent under a reduced pressure, 1N hydrochloric acid aqueous solution was added, and the mixture was extracted with chloroform and dried over anhydrous magnesium sulfate. After evaporation of the solvent under a reduced pressure, the resulting residue was recrystallized from ethyl acetatehexane to obtain 633 mg of (Z)-[4,4-difluoro-1-[4-(2-phenylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetic acid.

Workup

  1. additionwas added dropwise to the above solution under ice-
  2. temperaturecooling
  3. customAfter evaporating the solvent under a reduced pressure, 1N hydrochloric acid aqueous solution
  4. additionwas added
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter evaporation of the solvent under a reduced pressure
  8. customthe resulting residue was recrystallized from ethyl acetatehexane

Sources & evidence

ORD record
ord-0ac6d333e3e14c50b4391bf4f72bbef0
Source dataset
uspto-grants-1998_01
Patent number
US05710150

Reaction notes

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