Sulfuric Acid → HCID 10672079, compound
Reaction equation
[Br:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[F:12][C:13]1[C:14]([CH2:46]O)=[C:15]([F:45])[C:16]2[O:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([NH:28]C(=O)C(C)(C)C)=[C:24]([F:35])[CH:23]=3)=[CH:19][C:18](=[O:36])[C:17]=2[C:37]=1[NH:38]C(=O)C(C)(C)C>>[NH2:38][C:37]1[C:17]2[C:18](=[O:36])[CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([NH2:28])=[C:24]([F:35])[CH:23]=3)[O:21][C:16]=2[C:15]([F:45])=[C:14]([CH2:46][O:5][C:4](=[O:6])[CH2:3][CH2:2][Br:1])[C:13]=1[F:12]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
7.65 g (50.0 mmol) of 3-bromopropionic acid and 1.5 mL of sulfuric acid were added to 504 mg (1.00 mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-hydroxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one obtained in EXAMPLE 118 (4), and the mixture was stirred at 100° C. for 10 minutes. The reaction solution was poured into 100 mL of ice-water and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:acetonitrile=19:1), to give 163 mg of Compound 160 (yield: 35%).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with an aqueous saturated solution of sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (chloroform:acetonitrile=19:1)
Sources & evidence
- ORD record
- ord-dc7f3f09716c4ce89a5bc223cff55090
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05539112
Reaction notes
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