Hydrochloric Acid → HCID 54562015, compound

HRID 1417709Notes

Reaction equation

HRID 1417709 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[CH:17]=[C:18]3[C:23](=[C:24]([Br:26])[CH:25]=2)[O:22][C:21]([CH3:28])([CH3:27])[CH2:20][CH:19]3[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[O:15])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+].Cl>CCO>[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[CH:17]=[C:18]3[C:23](=[C:24]([Br:26])[CH:25]=2)[O:22][C:21]([CH3:28])([CH3:27])[CH2:20][CH:19]3[C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)=[O:15])[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54111174HCID 54111174, compound2×

Product 1

HCID 54562015HCID 54562015, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-fluoro-4-[[(8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl)carbonyl]amino]-benzoate (Compound 221, 135 mg, 0.25 mmol) in EtOH (5 mL) was added 20% aqueous NaOH (2 mL). The reaction mixture was stirred at room temperature overnight and acidified to pH 4 with 10% aqueous HCl. The EtOH was removed under reduced pressure and ethyl acetate and water were added to the residue. The organic layer was separated and washed with saturated NaHCO3, saturated aqueous NaCl, and dried over MgSO4. Concentration under reduced pressure afforded 110 mg (86%) of the title compound as a colorless solid. 1H NMR δ (acetone-d6) 8.09 (1H, d, J=2.1 Hz), 7.91 (1H, t, J=7.5 Hz), 7.68 (1H, d, J=2.1 Hz), 7.83 (1H, dd, J=12.8, 2.1 Hz), 7.50 (1H, dd, J=7.5 Hz, 2.1 Hz), 7.27 (4H, s), 5.87 (1H, s), 2.37 (3H, s), 1.56 (6H, s); MS (EI) m/e 511, 509, 496, 494, 452, 450, 357, 355, 312. Anal. (C26H21BrFNO4.0.6 H2O) C, H, N.

Workup

  1. customThe EtOH was removed under reduced pressure and ethyl acetate and water
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. washwashed with saturated NaHCO3, saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-6ac15e211d724ecaa8b20a59545f5eb1
Source dataset
uspto-grants-1999_03
Patent number
US05877207

Reaction notes

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