Sodium Hydroxide → HCID 10836335, compound

HRID 324222Notes

Reaction equation

HRID 324222 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[CH:25]=[CH:24][C:23]3[C:22]([CH3:27])([CH3:26])[CH2:21][CH:20]=[C:19]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)[C:18]=3[CH:17]=2)=[O:15])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>CCO.C1COCC1>[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[CH:25]=[CH:24][C:23]3[C:22]([CH3:27])([CH3:26])[CH2:21][CH:20]=[C:19]([C:28]4[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=4)[C:18]=3[CH:17]=2)=[O:15])[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10647511HCID 10647511, compound2×

Product 1

HCID 10836335HCID 10836335, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 41.6 mg (0.091 mmol) ethyl 2- fluoro-4-[[(5,6-dihydro-5,5-dimethyl-8- (4-methylphenyl)-2-naphthalenyl)carbonyl]amino]-benzoate (Compound 40) in 2.0 ml EtOH and 2.0 ml of THF was added 40.0 mg NaOH (1.00 mmol, 1.0 ml of a 1M aqueous solution). After stirring at room temperature for overnight, the reaction was quenched by the addition of 10% HCl. Extraction with EtOAc, and drying of the organic layers over MgSO4, provided a solid after removal of the solvent under reduced pressure. Crystallization from CH3CN afforded the title compound as a pale-yellow solid. 1H NMR (d6-acetone): δ 9.84 (1H, s), 7.94-7.83 (3H, m), 7.64 (1H, dd, J=2.0 Hz), 7.53 (2H, d, J=8.1 Hz), 7.23 (4H, s), 6.04 (1H, t, J=4.7 Hz), 2.38 (2H, d, J=4.7 Hz), 2.36 (3H, s), 1.35 (6H, s).

Workup

  1. customthe reaction was quenched by the addition of 10% HCl
  2. extractionExtraction with EtOAc
  3. dry with materialdrying of the organic layers over MgSO4
  4. customprovided a solid
  5. customafter removal of the solvent under reduced pressure
  6. customCrystallization from CH3CN

Sources & evidence

ORD record
ord-5fcfb87a8a2f4277b3d916c7123b26ca
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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