Sodium Hydroxide → HCID 10836335, compound

HRID 992525Notes

Reaction equation

HRID 992525 reaction equation
C([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:20]([CH3:25])([CH3:24])[CH2:19][CH:18]=[C:17]([C:26]4[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=4)[C:16]=3[CH:15]=2)=[O:13])=[CH:7][C:6]=1[F:33])C.[OH-].[Na+]>CCO.C1COCC1>[F:33][C:6]1[CH:7]=[C:8]([NH:11][C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:20]([CH3:25])([CH3:24])[CH2:19][CH:18]=[C:17]([C:26]4[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=4)[C:16]=3[CH:15]=2)=[O:13])[CH:9]=[CH:10][C:5]=1[C:4]([OH:34])=[O:3]

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) ethyl2-fluoro4-[[(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 1 M 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): δ9.84 (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-2e6981397bc6464199523376da4a52b7
Source dataset
uspto-grants-2002_10
Patent number
US06469028B1

Reaction notes

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