Water → HCID 19434874, compound

HRID 1736216Notes

Reaction equation

HRID 1736216 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21][CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C:11]=3[C:12](=[O:14])[CH:13]=2)=[CH:4][C:3]=1[F:28].S(=O)(=O)(O)[OH:30].O>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21][CH2:22][CH2:23][CH2:24][C:25]([OH:30])([CH3:26])[CH3:27])[C:11]=3[C:12](=[O:14])[CH:13]=2)=[CH:4][C:3]=1[F:28]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 19434909HCID 19434909, compound

Product 1

HCID 19434874HCID 19434874, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

16 mg (0.041 mmol) of Compound 137 obtained in Example 137 was dissolved in 3 mL of ethanol, 3 mL of 50% sulfuric acid was added and the mixture was stirred at 100° C. for 1 hour. The reaction solution was cooled on ice, water was added 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 to give 14 mg of Compound 138 (yield: 84%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. 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
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8b8cf33894cc4250b27616f1d3433195
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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