Hydrochloric Acid → HCID 68509093, compound

HRID 1715328Notes

Reaction equation

HRID 1715328 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][N:12]2[CH2:16][C:15]([CH3:18])([CH3:17])[CH:14]([O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=3)[C:13]2=[O:32])=[CH:9][CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH:14]2[C:15]([CH3:18])([CH3:17])[CH2:16][N:12]([CH2:11][C:8]3[O:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][CH:9]=3)[C:13]2=[O:32])=[CH:21][C:22]=1[C:28]([F:31])([F:30])[F:29])#[N:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 56670283HCID 56670283, compound

Product 1

HCID 68509093HCID 68509093, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 29, 5-[3-(4-cyano-3-trifluoromethyl-phenoxy)-4,4-dimethyl-2-oxo-pyrrolidin-1-ylmethyl]-furan-2-carboxylic acid ethyl ester, (0.461 g, 1.024 mmol) was dissolved in 5 mL THF and 1.5 mL 1 M NaOH was added. The reaction was stirred at ambient temperature overnight. The reaction mixture was acidified with 1 N HCl to pH ˜3 and extracted into ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the carboxylic acid, 5-[3-(4-cyano-3-trifluoromethyl-phenoxy)-4,4-dimethyl-2-oxo-pyrrolidin-1-ylmethyl]-furan-2-carboxylic acid, as a white solid (0.417 g).

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-820311f123e34f038c0ca967f4c05dee
Source dataset
uspto-grants-2010_09
Patent number
US07799823B2

Reaction notes

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