Sulfuric Acid → HCID 19434785, compound
Reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[C:8]([C:40]#[C:41][Si](C)(C)C)=[C:9]([F:39])[C:10]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([NH:22]C(=O)C(C)(C)C)=[C:18]([F:29])[CH:17]=3)=[CH:13][C:12](=[O:30])[C:11]=2[C:31]=1[NH:32]C(=O)C(C)(C)C>>[NH2:32][C:31]1[C:11]2[C:12](=[O:30])[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([F:29])[CH:17]=3)[O:15][C:10]=2[C:9]([F:39])=[C:8]([C:40]#[CH:41])[C:7]=1[F:6]Participants
3
Conditions
- Temperature
- 50 °C
Procedure
3 mL of concentrated sulfuric acid was added to 37 mg (0.065 mmol) of the above 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-7-(2-trimethylsilylethynyl)-4H-1-benzopyran-4-one and the mixture was stirred at 50° C. for 10 minutes. The reaction solution was poured into ice water and the mixture was extracted once with ethyl acetate. The organic layer was washed once with 1N aqueous solution of sodium hydroxide, once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sulfate. The solvent was distilled off under reduced pressure and the residue was purified by preparative thin layer chromatography (chloroform:acetonitrile=9:1) to give 15 mg of Compound 112 (yield: 70%).
Workup
- extractionthe mixture was extracted once with ethyl acetate
- washThe organic layer was washed once with 1N aqueous solution of sodium hydroxide, once with water and once with an aqueous saturated solution of sodium chloride
- dry with materialdried over anhydrous sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by preparative thin layer chromatography (chloroform:acetonitrile=9:1)
Sources & evidence
- ORD record
- ord-a59749666ab241e78106527bda9a5d24
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05539112
Reaction notes
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