Hydrochloric Acid → HCID 11291455, compound

HRID 1012355Notes

Reaction equation

HRID 1012355 reaction equation
[CH:1]1([C:7]2[C:8]3[C:13]([N:14]4[C:19]=2[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[S:16][CH2:15]4)=[CH:12][C:11]([C:24]([O:26]C)=[O:25])=[CH:10][CH:9]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCCC1.CO>[CH:1]1([C:7]2[C:8]3[C:13]([N:14]4[C:19]=2[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[S:16][CH2:15]4)=[CH:12][C:11]([C:24]([OH:26])=[O:25])=[CH:10][CH:9]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23152661HCID 23152661, compound

Product 1

HCID 11291455HCID 11291455, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 11-cyclohexyl-5-thia-6a-azabenzo[a]fluorene-8-carboxylate (100 mg, 0.26 mmol) in tetrahydrofuran (2 ml) and methanol (2 ml) was added 4N aqueous sodium hydroxide solution (2 ml), and the mixture was stirred at room temperature for 15 hr. 2N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1-1:1) to give 11-cyclohexyl-5-thia-6a-azabenzo[a]fluorene-8-carboxylic acid (32 mg, yield 33.3%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1-1:1)

Sources & evidence

ORD record
ord-c3d94eb3b0d5436d87d68c257f73e73a
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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