Potassium Carbonate → HCID 70161506, compound

HRID 1251090Notes

Reaction equation

HRID 1251090 reaction equation
[F:1][C:2]1([F:49])[CH2:3][CH2:4][N:5]([C:35]([C:37]2[S:41][C:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[N:39][C:38]=2[CH3:48])=[O:36])[C:6]2[CH:34]=[CH:33][CH:32]=[CH:31][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]([CH2:25][C:26]([O:28]CC)=[O:27])C(=O)C(F)(F)F)[CH2:14][CH2:13]1)=[O:11].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[F:49][C:2]1([F:1])[CH2:3][CH2:4][N:5]([C:35]([C:37]2[S:41][C:40]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[N:39][C:38]=2[CH3:48])=[O:36])[C:6]2[CH:34]=[CH:33][CH:32]=[CH:31][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][CH2:25][C:26]([OH:28])=[O:27])[CH2:14][CH2:13]1)=[O:11]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86757746HCID 86757746, compound

Product 1

HCID 70161506HCID 70161506, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 240 mg of ethyl (Z)-[(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)-(trifluoroacetyl)amino]acetate in 5 ml of ethanol was added a solution of 100 mg of potassium carbonate in 4 ml of water, and the mixture was stirred at 40° C. for 18 hours. After evaporation of the solvent, 1N hydrochloric acid was added to the residue, and the mixture was washed with ethyl acetate. The aqueous layer was neutralized and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of NaCl and dried over anhydrous magnesium sulfate, and the solvent was evaporated therefrom. The resulting residue was crystallized from diethyl ether to give 40 mg of (Z)-[(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)amino]acetic acid as a pale yellow powder.

Workup

  1. customAfter evaporation of the solvent, 1N hydrochloric acid
  2. additionwas added to the residue
  3. washthe mixture was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of NaCl
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe resulting residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-4f168256c82b4cbdb6e126e01d2958e7
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

Loading…