Sodium Hydroxide → (Z)-2-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetic acid

HRID 1251076Notes

Reaction equation

HRID 1251076 reaction equation
[OH-].[Na+].[F:3][C:4]1([F:34])[CH2:5][CH2:6][N:7]([C:20]([C:22]2[S:26][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:24][C:23]=2[CH3:33])=[O:21])[C:8]2[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=2/[C:10]/1=[CH:11]/[C:12]([O:14]C)=[O:13]>CO>[F:34][C:4]1([F:3])[CH2:5][CH2:6][N:7]([C:20]([C:22]2[S:26][C:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:24][C:23]=2[CH3:33])=[O:21])[C:8]2[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=2/[C:10]/1=[CH:11]/[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15552381methyl (Z)-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetate

Product 1

HCID 70160918(Z)-2-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1N aqueous solution of sodium hydroxide (5 ml) was added to a solution of 1,080 mg of methyl (Z)-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetate in 30 ml of methanol, followed by stirring at room temperature for 18 hours. After evaporating the reaction solution, 20 ml of water and 10 ml of 1N hydrochloric acid were added to the residue, and the resulting precipitate was collected by filtration and washed with water to give 1,000 mg of (Z)-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetic acid as a colorless powder.

Workup

  1. customAfter evaporating the reaction solution, 20 ml of water and 10 ml of 1N hydrochloric acid
  2. additionwere added to the residue
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-0c27fbbac674419297c3922bb840aac8
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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