Water → HCID 54142543, compound

HRID 1417701Notes

Reaction equation

HRID 1417701 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)=[S:15])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+].O.CCOC(C)=O>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)=[S:15])[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 54013279HCID 54013279, compound2×

Product 1

HCID 54142543HCID 54142543, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 46.5 mg (0.098 mmol) ethyl 2-fluoro-4-[[(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl)thiocarbonyl]amino]-benzoate (Compound 62) in 1.0 ml EtOH and 1.0 ml of THF was added 55 mg NaOH (1.4 mmol) and 1.0 ml of H2O. After stirring at room temperature for overnight EtOAc was added, and the reaction quenched by the addition of 10% HCl. Extraction with EtOAc was followed by washing of the combined organic layers with H2O, saturated aqueous NaCl, and drying over MgSO4. Removal of the solvent under reduced pressure provided a solid which after crystallization from CH3CN afforded the title compound as a pale-yellow solid. 1H NMR (d6 -acetone): δ 11.05 (1H, s), 8.02 (1H, m), 7.99 (1H, t, J=8.3 Hz), 7.75 (1H, m), 7.69 (1H, dd, J=2.0, 6.1 Hz), 7.52 (1H, s), 7.46 (1H, d, J=8.1 Hz), 7.21 (4H, m), 6.04 (1H, t, J=4.8 Hz), 2.37 (2H, d, J=4.8 Hz), 2.33 (3H, s), 1.36 (6H, s).

Workup

  1. additionwas added
  2. customthe reaction quenched by the addition of 10% HCl
  3. extractionExtraction with EtOAc
  4. washby washing of the combined organic layers with H2O, saturated aqueous NaCl
  5. dry with materialdrying over MgSO4
  6. customRemoval of the solvent under reduced pressure
  7. customprovided a solid which
  8. customafter crystallization from CH3CN

Sources & evidence

ORD record
ord-65b4ecbd8201414d89bb2174ecf07930
Source dataset
uspto-grants-1999_03
Patent number
US05877207

Reaction notes

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