Sodium Hydroxide → HCID 22228186, compound

HRID 1744578Notes

Reaction equation

HRID 1744578 reaction equation
C([CH:3]([C:33]([OH:35])=[O:34])[N:4]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:21]([C:31]#[N:32])[CH:20]=1)[C:5]([C:7]1[N:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)=[O:6])C.[OH-].[Na+]>C(O)C>[C:31]([C:21]1[CH:20]=[C:19]([N:4]([C:5]([C:7]2[N:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:10][CH:11]=2)=[O:6])[CH2:3][C:33]([OH:35])=[O:34])[CH:24]=[CH:23][C:22]=1[N:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)#[N:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22227876HCID 22227876, compound

Product 1

HCID 22228186HCID 22228186, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-(3-cyano-4-piperidinophenyl)-N-[1-(4-fluorophenyl)pyrrol-2-ylcarbonyl]glycine (1.0 g) was added to ethanol (10 ml), and 10% aqueous sodium hydroxide solution (10 ml) was added. The mixture was stirred at a refluxing temperature for 30 min. The solvent was evaporated under reduced pressure. Dilute hydrochloric acid was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. A mixed solvent of toluene-diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from hydrous methanol to give the title compound (0.5 g), melting point: 117–120° C.

Workup

  1. additionwas added
  2. customThe solvent was evaporated under reduced pressure
  3. additionDilute hydrochloric acid was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent was evaporated under reduced pressure
  8. additionA mixed solvent of toluene-diisopropyl ether was added to the residue
  9. customcrystallization
  10. customThe crystals were recrystallized from hydrous methanol

Sources & evidence

ORD record
ord-80fae38f4c7f4ebf936304ceec292b46
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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