Water → HCID 19434909, compound

HRID 1736215Notes

Reaction equation

HRID 1736215 reaction equation
C(OC([N:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[C:25]([NH:31][CH2:32][CH2:33][CH:34]=[C:35]([CH3:37])[CH3:36])[C:21]=3[C:22](=[O:24])[CH:23]=2)=[CH:14][C:13]=1[F:38])COC)=O)(C)(C)C.S(=O)(=O)(O)O.O>C(O)C>[NH2:8][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[C:25]([NH:31][CH2:32][CH2:33][CH:34]=[C:35]([CH3:36])[CH3:37])[C:21]=3[C:22](=[O:24])[CH:23]=2)=[CH:14][C:13]=1[F:38]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 194348222-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl]-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-one

Product 1

HCID 19434909HCID 19434909, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.03 g (1.94 mmol) of the above 2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl]-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-one was dissolved in 80 mL of ethanol, 20 mL of 50% sulfuric acid was added and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction solution and the mixture was extracted twice with ethyl acetate. The organic layer was washed once with an aqueous saturated solution of sodium bicarbonate, once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2-2:1) to give 520 mg of Compound 137 (yield: 69%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe organic layer was washed once with an aqueous saturated solution of sodium bicarbonate, once with water and once with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2-2:1)

Sources & evidence

ORD record
ord-64dbb16da52541278155aaf404452d68
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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